All issues
Volume 31, Issue 9
Displaying 1-50 of 56 articles from this issue
-
YUTAKA SAITO, JUNICHI ODO, MASAAKI NISHIO, YOSHIMASA TANAKA, KATSUNOSU ...1983 Volume 31 Issue 9 Pages 2967-2975
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe infrared spectra of trans- and cis-[bis (D-alaninato) copper (II)]n and their isotopic complexes containing 63Cu, 65Cu and deuterium were measured in the region between 4000 and 200 cm-1. By referring to the isotope shifts on deuteration and 63Cu and 65Cu substitution, the bands around 370 and 320 cm-1 were assigned to the Cu-N and the Cu-O asymmetric stretching vibrations, respectively, for both the trans and cis complexes. The magnitudes of the copper isotope shifts are consistent with those calculated from the normal coordinate analysis by using a complete molecular conformation and an intermolecular force field. The trans-isomer showed three copper isotope sensitive bands, while the cis-isomer showed two.View full abstractDownload PDF (834K) -
SABURO SHIMABAYASHI, MASAYUKI NAKAGAKI1983 Volume 31 Issue 9 Pages 2976-2985
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe amount of concurrent adsorption (i. e. co-adsorption) of Ca2+ and OH- on hydroxyapatite (HAP) was determined. It was found that the amount of adsorption of OH- (or Ca2+) increases linearly with that of the other co-adsorbate, Ca2+ (or OH-). Analysis of the data showed that there are two different adsorption sites on the surface of HAP : one is for individual ionic adsorption and the other is for ion-exchange and neutralization of proton. The adsorption isotherms for OH- (or Ca2+) were reduced to one curve when they were displaced somewhat in parallel with a straight line of slope -1, taking the adsorbed amount of co-adsorbate, Ca2+ (or OH-), into consideration. Adsorption of OH- and Ca2+ and/or coordination of Ca2+ to the surface phosphate on HAP are considered to be similar to what occurs during the crystal growth of HAP.View full abstractDownload PDF (926K) -
TOSHIKAZU NOZOYE, YOSHIHISA SHIBANUMA, TATSUYA NAKAI1983 Volume 31 Issue 9 Pages 2986-2992
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUpon being warmed at 90°C in trifluoromethanesulfonic acid for 42-78 h, 2-hydroxytryptophol (4a) gave 3-ethylideneoxidoles (E-and Z-form) (5a), while 3-methyl-(4b) or 3-ethyl-2-hydroxytryptophol (4c) gave the corresponding 3-alkylideneoxindoles (5b, 5c) and 3, 4-dialkylcarbostyrils (61-b, c, 6H-c). On tosylation in pyridine, 4a gave spiro-(3)-cyclopropane-(8) and 3-chloroethyl-oxindole (10), and the corresponding tosylate (7a), but 4b and 4c gave only the corresponding tosylates (7b, 7c). The tosylate 7a and the chloroethyl compound 10 reacted in alkaline ethanol to afford the spiro compound 8, whereas the tosylates 7b, 7c gave 2-ethoxy-3-methyl (or ethyl)-3-hydroxyethylindolenines (9b, 9c) under the same conditions.View full abstractDownload PDF (602K) -
TAKESHI DEYAMA1983 Volume 31 Issue 9 Pages 2993-2997
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new lignan diglycoside was isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae) and its structure was established as (+)-medioresinol di-O-β-D-glucopyranoside (1) by means of chemical and spectral studies. (+)-Pinoresinol di-O-β-D-glucopyranoside (2), liriodendrin (3) and (+)-pinoresinol O-β-D-glucopyranoside (4) were also isolated.View full abstractDownload PDF (598K) -
SETSUKO SEKITA1983 Volume 31 Issue 9 Pages 2998-3001
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo kinds of bis (3-indolyl)-dihydroxybenzoquinones, isocochliodinol and neocochliodinol, were isolated from Chaetomium murorum and C. amygdalisporum, respectively, and their structures were determined.View full abstractDownload PDF (501K) -
HISAKAZU MORI, KAZUYUKI MINETA, TAKAO KWAN1983 Volume 31 Issue 9 Pages 3002-3008
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe carboxylation of indene by carbon dioxide was investigated in the presence of substituted phenoxides in DMF. The reaction took place rapidly at 0°C and was apparently completed within about ten minutes. Indene-3-carboxylic acid was found to be formed in 42-98% yields from indene, depending on the substituents (p-OC4H9, p-OCH3, p-CH3, H, p-Cl, m-Cl, p-CN, and m-NO2) of the phenoxides. The substituent effect upon the interaction of carbon dioxide with the substituted phenoxides was observed. It was found that the yield of indene-3-carboxylic acid increased with substituents of negative σ values, giving rise to a linear relation between the logarithm of the equilibrium constants of carboxylation of indene and the σ values. Relative rates of reaction were compared with the various substituted phenoxides mentioned above. The mechanism of the reaction is briefly discussed.View full abstractDownload PDF (668K) -
YOSHIHISA KURASAWA, YUJIRO MORITAKI, MITSUGU ICHIKAWA, MIE OGURA, ATSU ...1983 Volume 31 Issue 9 Pages 3009-3013
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 3-methoxycarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxaline (1) with N-bromosuccinimide, N-chlorosuccinimide, Br2-H2O, and Cl2-H2O gave 4-halogeno-3-methoxycarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines (3a and 3b), while the reactions of 1 with H2O2-HBr and H2O2-HCl afforded 4-halogeno-3-(1-halogeno-1-methoxycarbonyl)-methylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines (4a and 4b). Mechanisms are proposed for these halogenations.View full abstractDownload PDF (550K) -
KEIICHI ITO, JUNKO MARUYAMA1983 Volume 31 Issue 9 Pages 3014-3023
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a new type of stable diazoalkane, 4-diazomethylcoumarins (4) bearing various 7-substituents were prepared for potential use in introducing fluorophores into acidic substances. Selenium dioxide oxidation of 4-methylcoumarins to the corresponding coumarin-4-carbaldehydes followed by triethylamine-mediated Bamford-Stevens reaction of their tosylhydrazones readily gave 4 as excellently stable and almost non-fluorescent crystals, exhibiting characteristic diazomethyl 1H- and 13C-nuclear magnetic resonance signals. Labeling reactions of carboxylic acids using 4 in refluxing chloroform in the presence of silica gel catalyst gave excellent yields of fluorescent coumarin-4-ylmethyl esters. In view of their stability, accessibility and fluorogenicity, these compounds (4), especially those bearing 7-methoxy and 7-acetyloxy substituents, should be practically useful fluorogenic reagents for carboxylic acids.View full abstractDownload PDF (893K) -
HISASHI ISHII, TSUTOMU ISHIKAWA, TAKEO DEUSHI, KENICHI HARADA, TOSHIKO ...1983 Volume 31 Issue 9 Pages 3024-3038
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the sake of establishment of a versatile synthetic method for benzo [c] phenanthridine alkaloids, improvement of the Robinson synthetic method was examined. Thirteen chalcones (7a-m) were prepared by condensation of two acetophenone derivatives (15 and 16) with eleven benzaldehyde derivatives (19a-k) as fundamental starting materials. Hydrocyanation of these chalcones (7a-l) except one (7m) gave the corresponding 2, 4-bisaryl-4-oxobutyronitriles (8a-l). Eleven 2, 4-bisaryl-4-oxobutyramides (9a-k) were also prepared.View full abstractDownload PDF (1664K) -
HISASHI ISHII, ERI KAWANABE, KENICHI HARADA, TAKEO DEUSHI, ETSUKO UEDA ...1983 Volume 31 Issue 9 Pages 3039-3055
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthetic pathway from 2, 4-bisaryl-4-oxobutyramide (3) to 2-aryl-1-tetralone (4), which is the key intermediate in the Robinson synthesis of antitumor-active benzo [c] phenanthridine alkaloids was improved. Treatment of the model keto-amide (3a) under the reported basic conditions gave a γ-keto-α, β-unsaturated acid (9) and degradation products. Reduction of the 2, 4-bisaryl-4-oxobutyramide (3) with sodium borohydride gave 2, 4-bisaryl-4-hydroxybutyramide (16), which could easily be hydrogenolyzed to give 2, 4-bisarylbutyramide (15). However, this transformation also tended to give a γ-lactam derivative (17), unfortunately. We succeeded in the direct hydrogenolysis of the 2, 4-bisaryl-4-oxobutyramide (3) to the 2, 4-bisarylbutyramide (15), which could be hydrolyzed to the corresponding acid (5) without difficulty. The direct hydrolysis of the 2, 4-bisaryl-4-oxobutyronitrile (2) to the 2, 4-bisaryl-4-oxobutyric acid (6) as reported by Cheng et al. was also examined. Ten 2-aryl-1-tetralones (4) required as starting materials for syntheses of various benzo [c] phenanthridine alkaloids were prepared.View full abstractDownload PDF (1913K) -
HISASHI ISHII, TAKEO DEUSHI, MITSUGI SAKAMOTO, KEIKO NAKAJIMA, TOSHIAK ...1983 Volume 31 Issue 9 Pages 3056-3073
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to establish a general preparative method for 2-aryl-1-formamido-1, 2, 3, 4-tetrahydronaphthalene derivatives from 2-aryl-1-tetralones, various methods were examined with 6, 7-methylenedioxy-2-(3, 4, 5-trimethoxyphenyl)-3, 4-dihydronaphthalen-1 (2H)-one as a model compound.View full abstractDownload PDF (1772K) -
JUTARO OKADA, KOICHI NAKANO, HIROSHI MIYAKE1983 Volume 31 Issue 9 Pages 3074-3083
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-(Substituted thiomethyl)-6-carbamoyluracils (IIIb-h) and 5-(substituted thiomethyl)-uracils (Va-h) were prepared and their ability to inhibit the growth of L-1210 cells in vitro was examined. The reaction of silylated furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VI) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VII) in acetonitrile in the presence of SnCl4 gave 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (VIII) in 81.0% yield. The protected nucleoside (VIII) was hydrolyzed by sodium methoxide to give the N1-nucleoside (X).View full abstractDownload PDF (763K) -
HIROSHI FURUKAWA, MOTOI YOGO, TIANSHUNG WU1983 Volume 31 Issue 9 Pages 3084-3090
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 13C-nuclear magnetic resonance spectra of twenty-seven acridone alkaloids including angular pyrano [2, 3-c] acridones and linear pyrano [3, 2-b] acridones have been analyzed and assigned. The information should be useful for the structure elucidation of new acridone alkaloids.View full abstractDownload PDF (629K) -
MASAKO TAKANI, YASUKO TAKASU, KOTARO TAKAHASHI1983 Volume 31 Issue 9 Pages 3091-3093
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new oxoisoaporphine-type compound, named dauriporphine, was isolated from the vines of Menispermum dauricum DC. (Menispermaceae) and the structure of this compound was elucidated as 4, 5, 6, 9-tetramethoxy-7H-dibenzo [de, h] quinolin-7-one (I).View full abstractDownload PDF (441K) -
NORIYA OHTA, YOSHIO OKADA, KEIICHI TANAKA1983 Volume 31 Issue 9 Pages 3094-3103
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight kinds of cysteine-containing peptides related to human hepatic metallothionein were synthesized by conventional methods. The metal-binding properties of these peptides with Zn2+ and Cd2+ were indicated by an increase of ultraviolet absorbance resulting from mercaptide formation. The Cd-binding activities of various peptides obtained here were assessed by measuring the increase in absorbance of mercaptide at 250 nm as a function of the concentration of Cd. The binding abilities of the peptides with Cd differed substancially.View full abstractDownload PDF (1070K) -
MASAMI SHIMAZAKI, HIKARU NAKAMURA, YOICHI IITAKA, MASAJI OHNO1983 Volume 31 Issue 9 Pages 3104-3112
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA stereoselective photoaddition of methanol to nebularine and 2', 3', 5'-tri-O-acetylnebularine was investigated. The absolute stereochemistry of the nebularine-methanol photoadduct (2a), a potential transition-state analog of adenosine deaminase, was determined to be 6 (S) by X-ray analysis. The addition site of methanol on the purine ring was also chemically demonstrated to be at C (6).View full abstractDownload PDF (924K) -
MASAMICHI FUKUOKA, KUNITOSHI YOSHIHIRA, SHINSAKU NATORI, KUNIHIDE MIHA ...1983 Volume 31 Issue 9 Pages 3113-3128
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethyl derivatives of indan-1-one were prepared as models to aid in interpreting the carbon-13 nuclear magnetic resonance (13C-NMR) spectra of pterosin-sesquiterpenes which were isolated from bracken fern, Pteridium aquilinum var. latiusculum. The chemical shifts of the carbons of the methylindan-1-ones were assigned by the proton decoupling technique. All the 13C-NMR signals of the pterosin-sesquiterpenes were assigned by means of selective proton decouplings, and from the 13C-1H long-range couplings and 13C chemical shifts of the model compounds..View full abstractDownload PDF (1265K) -
MACHIKO ONO, SHIGENORI OHTSUKA, SHINZO TAMURA1983 Volume 31 Issue 9 Pages 3129-3138
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reversible acid-catalyzed hydrolysis of β-arylaminoacrolein (I) has been studied kinetically. The kinetic runs were carried out in 1% aqueous ethanol in the presence of hydrochloric acid or acetic acid as well as in acetate buffer solutions at 25°C. The Hammett plot for the equilibrium constant K was linear. The value of log K was expressed by the equation log K=1.38σ-5.55. The loss of arylamine from the carbinolamine intermediate was rate-determining under strongly acidic conditions, while the rate of attack of water at the β-position of I was comparable to that of loss of arylamine from the intermediate under weakly acidic conditions. The reaction suffered general acid catalysis. The solvent-catalyzed term and catalytic constants for hydronium ion and for acetic acid were evaluated for both steps. General acid catalysis of acetic acid was of minor importance for the attack of water on I. The Hammett plot for the rate of reaction of water and conjugate acid of I was linear. The value of log kH1KBH+ was expressed by the equation log kH1KBH+=0.468σ-1.08. The reaction mechanism is discussed.View full abstractDownload PDF (748K) -
NOBUTAKA KAWAI, NOBUHARU KATO, YASUMASA HAMADA, TAKAYUKI SHIOIRI1983 Volume 31 Issue 9 Pages 3139-3148
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of diphenylphosphinic azide (8) with the pyrrolidine enamine 13 of 4-isobutylpropiophenone afforded two amidines 15a and 16a, which were derived from the 1, 3-dipolarcycloadduct 14a by the expulsion of nitrogen followed by 1, 2-aryl migration (path a) and by 1, 3-dipolar elimination (path b), respectively. Although diphenylthiophosphinic azide (9) and ethyl phenylthiophosphonoazidate (10) also gave similar results, diphenyl phosphorazidate (DPPA, (C6H5O)2P(O)N3) furnished the amidine 15d formed via path a as the sole isolable product. Hydrolysis of 15d with potassium hydroxide afforded ibuprofen (3) in good yield. Other nonsteroidal antiinflammatory agents, naproxen (4), ketoprofen (5), and flurbiprofen (6), were analogously and conveniently prepared from the ketones 17, 22, and 25, respectively, by a similar three-step operation using pyrrolidine, DPPA, and potassium hydroxide. 2-(2-Dibenzofuranyl)-propionic acid (7) was also prepared from the ketone 28 by the three-step procedure.View full abstractDownload PDF (982K) -
TOZO FUJII, TAISUKE ITAYA, FUMIKO TANAKA, TOHRU SAITO, KAZUYO MOHRI, K ...1983 Volume 31 Issue 9 Pages 3149-3159
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the effect of the N6-methoxy group on the site of methylation, N6-methyl-(27), 1-methyl-(17), 3-methyl-(11), 7-methyl-(7), and 9-methyl-N6-methoxyadenine (2) were methylated with an excess of MeI in AcNMe2. The products isolated were the 3-methylated product 12·HClO4 (67%yield) and 9-methylated product 3 (18%) from 27 ; 3-methylated product 15 (X=I) (44%) and 9-methylated product 18·HClO4 (38%) from 17 ; 15 (X=I) (40%) and 12·HClO4 (36%) from 11 ; 9-methylated product 5 (X=I) (36%) and 3-methylated product 8 (44%) from 7 ; 5 (X=I) (59%) and 3·HI (24%) from 2. Further methylation of 18 in a similar manner was found to give N6-methoxy-1, 7, 9-trimethyladeninium iodide (33 : X=I) in 92% yield. A similar methylation of the betaine 32, generated from 5 (X=I) by treatment with 1, 8-diazabicyclo [5. 4. 0] undec-7-ene (DBU), also produced 33 (X=I) in fair yield. The 7, 9-dimethyl derivative 5 (X=I) thus obtained was converted into the perchlorate 5 (X=ClO4), and hydrogenolysis of 5 (X=ClO4) using Pd-C and hydrogen furnished hitherto unknown 7, 9-dimethyladeninium perchlorate (6 : X=ClO4) in good yield. The substrates 11 and 27 used for the methylation study were prepared in 87 and 86% yields from 3-methyl-6-methylthiopurine (10) and 6-chloropurine (26) by amination with methoxyamine and N, O-dimethylhydroxylamine, respectively. For the synthesis of the substrate 17, 1-methoxyadenosine (25) was methylated to give the N6-methyl derivative 23. Treatment of 23 with hot water and hydrolysis of the resulting isomer 21 with 98% formic acid afforded the desired compound 17.View full abstractDownload PDF (1248K) -
JEANCHARLES LANCELOT, SYLVAIN RAULT, NGUYEN HUY DUNG, MAX ROBBA1983 Volume 31 Issue 9 Pages 3160-3167
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthesis of pyrido [2, 3-h] pyrrolo [1, 2-a] quinoxaline derivatives is described, starting from 5-amino-6-nitroquinoline. The pyrrole ring is obtained by reaction with 2, 5-dimethoxytetrahydrofuran. Cyclization of the pyrazine ring is achieved after reduction of the nitro grouping by intramolecular cyclization of 6-amino-5-(1-pyrrolyl) quinoline derivatives. 1H nuclear magnetic resonance spectra are studied.View full abstractDownload PDF (862K) -
YASUO ISOMURA, NORIKI ITO, HIROSHIGE HOMMA, TETSUSHI ABE, KAZUO KUBO1983 Volume 31 Issue 9 Pages 3168-3178
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA number of 2, 6-di-tert-butylphenols with a heterocyclic group at the 4-position were prepared. The heterocyclic groups were as follows : benzoxazole, benzothiazole, benzimidazole, indole, imidazo [1, 2-a] pyridine and imidazo [1, 2-a] pyrimidine. Anti-inflammatory activity of these compounds was examined by using the adjuvant-induced arthritis (A. A) assay. Some compounds were further tested in carrageenin-induced rat paw edema (CIPE) assay and AcOH-induced writhing (AIW) assay in mice. The anti-inflammatory activity was greatly dependent on the value of the heterocyclic group. Among these compounds, 2-(3, 5-di-tert-butyl-4-hydroxyphenyl)-benzoxazole (IIa) and 2-(3, 5-di-tert-butyl-4-hydroxyphenyl) indole (Xg) showed very potent activity. Both IIa and Xg had a minimum effective dose of 5 mg/kg (p. o.) in A. A assay and showed stronger activity than phenylbutazone in CIPE assay but weaker analgesic activity than aminopyrine in AIW assay.View full abstractDownload PDF (810K) -
YASUO ISOMURA, NORIKI ITO, SHUICHI SAKAMOTO, HIROSHIGE HOMMA, TETSUSHI ...1983 Volume 31 Issue 9 Pages 3179-3185
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 6-Di-tert-butylphenols with an imidazo [2, 1-b] thiazole or 2, 3-dihydroimidazo [2, 1-b] thiazole group at the 4-position were prepared. Substituents were introduced at the 5-position of 6-(3, 5-ditert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole (Ia) by means of the Vilsmeier reaction and Mannich reaction. 6-(3, 5-Di-tert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole 1-oxide (IVa) and the 1, 1-dioxide (IVb) were obtained by oxidation of Ia. The above compounds were examined for anti-inflammatory activity in adjuvant-induced arthritis in rats, and some compounds were further tested for activity in the carrageenin-induced rat paw edema assay and in the AcOH-induced writhing assay in mice. Some of the compounds showed potent anti-inflammatory and analgesic activities. The most potent compound, IVa (25 mg/kg, p. o.), had about the same anti-inflammatory activity as indomethacin (2 mg/kg, p. o.), but IVa (50 mg/kg, p. o.) had weaker analgesic activity than aminopyrine (50 mg/kg, p. o.).View full abstractDownload PDF (636K) -
HIROYUKI OBASE, NOBUHIRO NAKAMIZO, HARUKI TAKAI, MASAYUKI TERANISHI, K ...1983 Volume 31 Issue 9 Pages 3186-3197
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe synthesized a series of arylalkyl piperidines (II) carrying a heterocycle at the 4-position of piperidine and examined the hypotensive activities of the products. Compound 23 had the highest hypotensive activity in anesthetized normotensive rats (-78 mmHg, 30 mg/kg, i.p.) and compound 12 showed the strongest hypotensive activity (-95 mmHg, 30 mg/kg, p.o.) in unanesthetized spontaneously hypertensive rats. Only compound 16 produced a considerable decrease in blood pressure in both animal models.View full abstractDownload PDF (1033K) -
TAICHI OHMOTO, KAZUO KOIKE1983 Volume 31 Issue 9 Pages 3198-3204
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new alkaloids, 4, 9-dimethoxy-1-vinyl-β-carboline (XI) and β-carbolin-1-yl 3-(4, 8-dimethoxy-β-carbolin-1-yl)-1-methoxypropyl ketone (XII) were isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae) together with known alkaloids, 1-ethyl-4-methoxy-β-carboline (VI), 4-methoxy-1-vinyl-β-carboline (VII), 4, 8-dimethoxy-1-vinyl-β-carboline (VIII), canthin-6-one (IX), and 5-methoxycanthin-6-one (X). The structures of these alkaloids were elucidated on the basis of spectroscopic evidence.View full abstractDownload PDF (569K) -
TOSHINOBU MORITA, RYOJI KASAI, HIROSHI KOHDA, OSAMU TANAKA, JUN ZHOU, ...1983 Volume 31 Issue 9 Pages 3205-3209
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom rhizomes of Panax japonicus collected in Yunnan, China (Chinese name : Zhujie-Shen), various oleanolic acid saponins, chikusetsusaponins-IVa (1), -IV (7) and -V (2) were isolated in high yields, together with the methyl ester of 2. All these compounds have already been isolated from rhizomes of the same species of Japanese (Japanese name : Chikusetsu-Ninjin) and Himalayan Panax (P. pseudo-ginseng WALL. subsp. himalaicus HARA). On the other hand, dammarane saponins of Zhujie-Shen were found to consist of ginsenosides-Rd (3), -Re (9), -Rg1 (10), -Rg2 (11), notoginsenoside-R2 (4) and pseudo-ginsenoside-F11 (13), being significantly different from those of Chikusetsu-Ninjin and Himalayan Panax. No characteristic morphological difference in external or internal structures was observed between the Chinese and Japanese specimens.View full abstractDownload PDF (576K) -
HIROTERU SAYO, MIKIO HOSOKAWA1983 Volume 31 Issue 9 Pages 3210-3213
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA deuterated spin-labeled derivative of cortisol (F3-SLD) was prepared by coupling cortisol-3-(O-carboxymethyl) oxime with 4-amino-1-oxyl-2, 2, 6, 6-tetramethylpiperidine-d17 and used to improve the sensitivity of spin immunoassay (SIA) of cortisol. The linewidth of the high-field peak of F3-SLD was 1.4G at the modulation amplitude (Hm) of 1.6G, and that of the undeuterated spin-label was 1.9G at Hm=2.0G. When 200 μl of cortisol standards was used for the assay, the minimum detectable concentration of cortisol was reduced from 10 ng/200 μl to 2.5 ng/200 μl by the use of F3-SLD. Although the increase in the sensitivity of SIA is not yet sufficient, the use of deuterated spin-labels is considered to be useful for enhancing SIA sensitivity.View full abstractDownload PDF (500K) -
YASUHIRO YAMANE, SHIZUO SAITO, TOSHIAKI KOIZUMI1983 Volume 31 Issue 9 Pages 3214-3221
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe cooperative inhibitory action of heparin and antithrombin III on the thrombinfibrinogen reaction was neutralized by preincubating these anticoagulant factors in the presence of Ca or Mg, and the effect was larger with Ca than with Mg. However, the neutralizing action of Ca decreased in the presence of Mg. Bindings of poly-L-lysine and antithrombin III to heparin were also inhibited by the addition of Ca and Mg, and Ca had a larger effect than Mg. On the other hand, the binding ability of Ca to heparin was larger than that of Mg, and the coexistence of these metals reduced the binding affinity of each metal. These data suggest that the neutralizing action of Ca and Mg on the anticoagulant action of heparin and antithrombin III may be related to the ability of these metals to prevent the complex formation of the acid mucopolysaccharide and the thrombin inhibitor by binding to the acid mucopolysaccharide.View full abstractDownload PDF (793K) -
MASATSUNE ISHIGURO, MASAKO MITARAI, HIROMICHI HARADA, ICHIRO SEKINE, I ...1983 Volume 31 Issue 9 Pages 3222-3227
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRats intoxicated orally with ricin (30mg/kg) showed clear signs of sickness and all died within 36 h. Dying animals shivered and lost body weight. The animals suffered from severe diarrhea within 5-10 h and profuse watery purging. In all intoxicated animals, large amounts of watery fluid were seen in the small intestine, but no significant changes in other organs were observed on gross examination. The effect of oral administration of ricin (30 mg/kg) on D-glucose absorption by rat small intestine was examined by the in vitro everted sac method. The amount of D-glucose absorbed by the small intestine derived from ricin-treated rats was 61.8 μg per 100 mg of tissue per hour or 30% of that of normal rats (206 μg/100 mg of tissue/h) at 5 h after intoxication. Absorptions of D-galactose, D-mannose, and 3-O-methylglucose by the small intestine of ricin-treated rats were 66, 46, and 80% of those of the normal intestine, respectively. Light microscopic examination revealed significant changes such as loss of villi and delay of the regeneration of absorptive epithelials of the small intestine at 5 h after administration. From these results, it was inferred that ricin acts primarily on the intestinal mucosa and impairs sugar absorption.View full abstractDownload PDF (751K) -
AKIHIKO KAWAGUCHI, YOKO KOBAYASHI, YUJI OGAWA, SHIGENOBU OKUDA1983 Volume 31 Issue 9 Pages 3228-3232
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method for the determination of double bond positions in polyunsaturated fatty acids is described. Double bonds in polyunsaturated fatty acids were reduced with deuteriodiimide and the resulting saturated fatty acids were converted to pyrrolidide derivatives. The location of deuterium atoms of the pyrrolidides were analyzed by gas chromatography-mass spectrometry. The positions of all the original double bonds could be deduced from mass fragment peaks containing deuterium atoms.View full abstractDownload PDF (529K) -
TOSHIO OKANO, SONOKO MASUDA, MASAKO ISHIMINE, JUNKO MURAI, YUKAKO YAMA ...1983 Volume 31 Issue 9 Pages 3233-3241
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe transport forms of vitamin D3 and 25-hydroxyvitamin D3 [25 (OH) D3] in lymph were studied in rats with thoracic duct cannulas. Under in vitro and in vivo conditions, the majority of vitamin D3 recovered from lymph was found in the chylomicrons and other lipoproteins fractions. On the other hand, the major fraction containing 25 (OH) D3 corresponded to the albumin and α-globulin fractions. In order to confirm the presence of binding protein having affinity to 25 (OH) D3 in lymph, the binding protein was isolated and purified by procedures of gel filtration, affinity and ion exchange chromatography from the incubated mixture of thoracic duct lymph with 25 (OH) D3. The purified binding protein showed a single band of protein on disc and sodium dodecyl sulfate-disc gel electrophoreses. Furthermore, the protein also gave a single peak on highperformance liquid chromatography (HPLC) using a gel permeation column. The molecular weight of the protein was calculated from the results of HPLC as 57000, a value which is apparently different from that of lymph albumin. These results suggest that vitamin D3 and 25 (OH) D3 are mainly transported from the intestine to the liver via the lymph duct by different carrier mediators as lipoprotein complex and protein-bound forms, respectively, in rats.View full abstractDownload PDF (924K) -
YOSHIHARU KARUBE, TAKESHI IMOTO, TATSUO MAEDA, MASATO OHYA, SETSURO SU ...1983 Volume 31 Issue 9 Pages 3242-3247
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTumor tissues were clearly visualized in scintigrams of experimental animals bearing tumors a few hours after the administration of 99mTc complex of ethylenediamine-N, N-diacetic acid. The animals used were mice bearing Ehrlich tumor, mice bearing Sarcoma 180, golden hamsters bearing lymphoma, mice bearing fibrosarcoma induced by 3-methylcholanthrene (MC), rats bearing MC-induced fibrosarcoma that had been transplanted at the limb and had spontaneously metastasized to the lung, and mice bearing spontaneous mammary carcinoma. In the mice bearing Ehrlich tumor, the ratios of radioactivity, tumor/blood and tumor/muscle, were 3.32 and 7.96, respectively, at 3 h after the administration.View full abstractDownload PDF (1941K) -
KAZUYUKI HIRANO, YUICHI IIIZUMI, MAMORU SUGIURA, JUN MIYAZAKI, KAZUMAS ...1983 Volume 31 Issue 9 Pages 3248-3254
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inactivation of human placental and intestinal alkaline phosphatases by sodium thiocyanate was investigated. Human placental alkaline phosphatase activity was completely inhibited by 2 M sodium thiocyanate, but human intestinal alkaline phosphatase was resistant to it. The structure of the inactivated enzyme was studied by means of the hydrophobic probe technique and circular dichroism method. Conformational changes had occurred in the secondary structure of the enzymes, and the hydrophobic regions of the inactivated enzymes had increased compared with those of the native enzymes. The addition of inorganic phosphate to the enzyme treatment system combined with sodium thiocyanate protected human placental alkaline phosphatase from inactivation, while human intestinal alkaline phosphatase was not protected. These findings suggest that the site attacked by sodium thiocyanate may be a region which induces conformational change upon binding of inorgaic phosphate at the active site in human placental alkaline phosphatase.View full abstractDownload PDF (735K) -
KUNIO NAKANISHI, MIKIO MASADA, TANEKAZU NADAI1983 Volume 31 Issue 9 Pages 3255-3263
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of Tween-type surfactants on the permeability of the rectal membrane was investigated by determining the absorption and apparent rectal clearance of marker drugs, using the in situ perfusion technique in rats. The tested substances were polysorbates 85, 80, 60, 40, 21, and 20, and polyoxyethylene sorbitan 20. When these surfactants were added in aqueous solutions, they did not significantly affect the permeability. On the other hand, these surfactants affected the histological nature of the rectal tissue and enhanced the permeability when they were added in oil.View full abstractDownload PDF (1431K) -
EIICHI KIMURA, ASUKA WATANABE, HIROMI NIHIRA1983 Volume 31 Issue 9 Pages 3264-3268
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe novel complexing properties of macrocyclic polyamines with phosphate and oxalate anions, which we previously discovered, were tested against urinary calculi. An 18-membered hexaamine [18] ane N6 and a 16-membered pentaamine [16] ane N5 in vitro solubilized inorganic models of calculi (Ca3 (PO4)2 and Ca (C2O4) and human urinary calculi in acidic solutions, implying that they may be useful as a new type of ingredient of irrigating fluids.View full abstractDownload PDF (563K) -
HSINGCHU HSU, JUN WATANABE1983 Volume 31 Issue 9 Pages 3269-3276
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe implication of thoracic duct lymph in the distribution and the elimination of rabbit muscle creatine phosphokinase (CPK) was investigated in situ and in vitro with 30 rabbits. The rate of thoracic duct lymph flow per kg body weight in anesthetized rabbits was 0.97±0.21 ml·h-1·kg-1 (mean±S. D., n=9). The CPK activity (U) that appeared in thoracic duct lymph after laparotomy (15 cm dissection along the mid-line) was 0.129±0.038 U/h (n=4) in untreated rabbits and 4.55±2.23 U/h (n=5) in rabbits given intramuscular administration of CPK (1000 U/kg body weight). The rate of transfer of CPK from the circulation to the thoracic duct lymph in rabbits after intravenous administration of CPK (1000 U/kg) was 30.0±11.1 U/h (n=5). The inactivation rate constant of CPK in thoracic duct lymph (pH 7.40, 39°C, 0.098±0.023h-1, n=5) was larger than that in heparinized whole blood. The result implies that CPK may be partly inactivated in the lymph in vivo. The inactivation rate constant of CPK in thoracic duct lymph fluid without lymphocytes (pH 7.40, 0.159±0.013h-1, n=3) was much larger than that in the thoracic duct lymph. The calcium concentration (14.4±0.810mg/dl, n=7) and the magnesium concentration (3.93±0.530mg/dl, n=7) in thoracic duct lymph were determined. The possible mechanism involved in the inactivation of CPK in thoracic duct lymph is discussed.View full abstractDownload PDF (838K) -
YUKIHIKO ARAMAKI, ASAICHI INABA, JUNJI NIIBUCHI, SEISHI TSUCHIYA1983 Volume 31 Issue 9 Pages 3277-3283
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe binding of three aminoglycoside antibiotics, gentamicin, amikacin, and 3', 4'-dideoxykanamycin B, to various lysosomal enzymes, N-acetyl-β-D-glucosaminidase, acid phosphatase, and lysozyme, was examined in vitro by using an affinity column of 3', 4'-dideoxykanamycin B-conjugated Sepharose 4B in order to investigate the mechanism of the accumulation of aminoglycoside antibiotics in the kidney. N-Acetyl-β-D-glucosaminidase and lysozyme were bound to the affinity column, but acid phosphatase was not adsorbed on the column. The activity of lysozyme was strongly inhibited by the addition of the three aminoglycosides at the concentration of 1 mM. In the case of N-acetyl-β-D-glucosaminidase, the activity was significantly inhibited in the presence of amikacin, but, in contrast, the activity was slightly activated by the addition of gentamicin or 3', 4'-dideoxykanamycin B. Acid phosphatase activity was not affected by the addition of any of the aminoglycosides. Lineweaver-Burk plots indicate that the inhibition of N-acetyl-β-D-glucosaminidase by amikacin is competitive. In the case of lysozyme, competitive inhibition by all three aminoglycosides was observed with Micrococcus luteus cells as the substrate. These findings indicate that the lysosomal enzyme activities may be influenced by the binding of aminoglycosides, and this binding may represent one of the accumulation mechanisms of aminoglycosides in the kidney.View full abstractDownload PDF (616K) -
KANETO UEKAMA, YUJI UEMURA, FUMITOSHI HIRAYAMA, MASAKI OTAGIRI1983 Volume 31 Issue 9 Pages 3284-3291
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe purpose of the present study was to assess two recently described models (S-Lw-Lo and S-Lw-in situ) for the prediction of drug absorption behavior in vivo following dissolution from a compressed tablet. The experiments were carried out by using 11 sulfonamides as test compounds to survey the validity of the models. In the S-Lw-Lo model, the drug appearance in the aqueous phase, Cw, and in the organic phase, Co, obeyed first order kinetics from 0 to 6 h. In the S-Lw-in situ model, the drug disappearance in the reservoir, (Cw-Ci)t, and change in blood levels of the drug, Cbt, with respect to time were analyzed simultaneously, and the factors affecting the drug absorption are discussed on the basis of the physicochemical and pharmacokinetic properties of the drug. It was found that the Cot value was significantly correlated with both (Cw-Ci)t and Cbt values. The Cot values were also correlated well with the blood levels of the drug in vivo following oral administration to rabbits. The results indicated that the two experimental models are useful to predict the absorption behavior of drugs and their usefulness may be extended to the evaluation of oral bioavailability.View full abstractDownload PDF (739K) -
YASUO MURAI, TERUMICHI NAKAGAWA, KIYOSHI YAMAOKA, TOYOZO UNO1983 Volume 31 Issue 9 Pages 3292-3301
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPharmacokinetic evaluations of cloxacillin and dicloxacillin in man were performed by detailed investigations of the urinary excretion profiles of the unchanged form and three metabolites (penicilloic acid, 5-hydroxymethyl derivative, and penicilloic acid of the 5-hydroxymethyl derivative). The last metabolite was newly found in human urine. The time course curves for excretion of unchanged form and the metabolites were measured by high performance liquid chromatography of urine excreted after oral administration of cloxacillin and dicloxacillin to human subjects. The values of cumulative excretion amount at infinite time (X∝u) and of mean residence time (MRT) for each species were estimated by moment analysis of excretion rate vs. time curves. The metabolic pathways of cloxacillin and dicloxacillin were assessed, and the transfer ratio at each elimination step and the MRT value intrinsic to each metabolite were evaluated from the results of moments. On the basis of these and the previous results for oxacillin and flucloxacillin, the pharmacokinetic features of four isoxazolylpenicillins are compared in terms of statistical moments. The extent and rate of total bioavailable activity due to the unchanged form and 5-hydroxymethyl metabolite are also discussed comparatively.View full abstractDownload PDF (920K) -
MASAHIRO MIYASHITA, YOSHIYUKI SEYAMA, SABURO YAMASHITA1983 Volume 31 Issue 9 Pages 3302-3305
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConditions for the synthesis and purification of monoiodocarnosine (MIC) were examined by high performance liquid chromatography (HPLC). When carnosine (β-alanyl-L-histidine) was iodinated to obtain MIC, the maximum yield was attained by the equimolar reaction of carnosine with I2 in 0.5 N NaOH solution. The synthesized MIC was separated by preparative reversedphase HPLC with H2O-MeOH (90 : 10) as the eluent and then purified by recrystallization. Chemically pure MIC was obtained in 72% yield in a short time.View full abstractDownload PDF (471K) -
ENKOU NAGASHIMA, KUNIO SUZUKI, MINORU SEKIYA1983 Volume 31 Issue 9 Pages 3306-3308
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present paper describes the reactions of two series of compounds, [chemical formula] and [chemical formula], with butyllithium. The former gives 1, 2-dithio-substituted acetylenes by rearrangement, whereas the latter gives cumulenes by dimerization.View full abstractDownload PDF (402K) -
MASANORI TERANISHI, YOUICHI FUJII, MITSURU YAMAZAKI, SUSUMU MIYABO1983 Volume 31 Issue 9 Pages 3309-3314
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDynamic aspects of methylation of catechol estrogen with diazomethane were investigated by means of thin-layer chromatography. The methylation rate of the hydroxyl group at the C-3 position was almost the same as that of the C-2 hydroxyl group in the reaction of 2-hydroxyestrogen, and 2-3 times that of the C-4 hydroxyl group in the reaction of 4-hydroxyestrogen. In these experiments, the maximum yields of 2-methoxyestrone, 2-hydroxyestrone 3-methyl ether, 4-methoxyestrone and 4-hydroxyestrone 3-methyl ether were 32, 39, 13 and 70%, respectively. In addition, demethylation of catechol estrogen dimethyl ethers with boron tribromide and synthesis of 4-hydroxyestrone monomethyl ethers are described.View full abstractDownload PDF (641K) -
SHIGEO YAMAMOTO, YOSHIKO AOYAMA, MIHO KAWAGUCHI, AKIMASA IWADO, MASAMI ...1983 Volume 31 Issue 9 Pages 3315-3318
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn unusual polyamine, sym-homospermidine, was identified in water hyacinth, Eichhornia crassipes SOLMS, by gas chromatography-mass spectrometry as its N-ethoxycarbonyl derivative. This polyamine predominated in the root and its contents determined by gas chromatography were in the range of 9.9-46.4 nmol/g fresh weight.View full abstractDownload PDF (483K) -
TSUTOMU KURODA, TERUYOSHI YOKOYAMA, TSUNEO UMEDA, ATSUKO MATSUZAWA, KO ...1983 Volume 31 Issue 9 Pages 3319-3325
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe plasma concentration of indomethacin (IM) after administration of sustained-release suppositories containing microencapsulated IM was analyzed by means of the compartment model method and the statistical moment method. The plasma concentration-time course after rectal administration of conventional suppositories followed a two-compartment model with first-order absorption for all doses examined, 6.25, 12.5 and 25 mg. The pharmacokinetic constants did not show dose-dependency. It was presumed that the plasma concentration-time course after rectal administration of sustained-release suppositories could be accounted for by a two-compartment model with two consecutive first-order input steps. The release rate constants (k1) of these dosage forms were very small compared with the absorption rate (ka). Consequently, the release process from sustainedrelease suppositories was the rate-determining step. This conclusion was confirmed by statistical moment analysis.View full abstractDownload PDF (569K) -
Hidetsura Cho, Masaru Ueda, Kazuteru Funahashi, Keiko Koda1983 Volume 31 Issue 9 Pages 3326-3329
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical modification in the hydrophilic and hydrophobic regions of leukotrienes was investigated in relation to their smooth muscle contractile activities. The conjugated diene or triene moiety in the hydrophobic region is crucial for potent contractile activity. The hydrophilic region at the C-6 position is not dependent only on amino acid or peptide for potent contractile activity ; some heterocyclic compounds can be used instead.View full abstractDownload PDF (386K) -
Hisashi Ishii, JunIchi Kobayashi, Tsutomu Ishikawa1983 Volume 31 Issue 9 Pages 3330-3333
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSToddalenone, a new coumarin, was isolated from Toddalia asiatica (L.) Lam. (T. aculeata Pers.). Its structure was established as the formula (1) by correlation with limettin (2). Vilsmeier-Haack formylation of limettin (2) gave 8-formyllimettin (10) in good yield. Aldol condensation of this material (10) with acetone afforded toddalenone (1).View full abstractDownload PDF (449K) -
Shigeyuki Kitamura, Kiyoshi Tatsumi1983 Volume 31 Issue 9 Pages 3334-3337
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present study provides the first evidence that rabbit liver aldehyde oxidase supplemented with its electron donors functions as an azoreductase towards azo compounds such as methyl red, amaranth, methyl orange and p-dimethylaminoazobenzene.View full abstractDownload PDF (407K) -
Shinichiro Sakai, Keiichi Yamaguchi, Ichiro Yamamoto, Katsumi Hotoda, ...1983 Volume 31 Issue 9 Pages 3338-3341
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new alkaloids, ryosenamine (I), ryosenaminol (II) and ibukinamine (III), were isolated from Aconitum ibukiense Nakai (ibuki torikabuto). The structure of ryosenamine (I) was elucidated as 1-deoxyhypognavine by spectroscopical study and determined by its correlation with ryosenaminol (II), the structure of the latter being confirmed by X-ray analysis. The structure of ibukinamine (III) was also determined by X-ray analysis.View full abstractDownload PDF (414K) -
Michihiko Noguchi, Hiroshi Kan, Shoji Kajigaeshi1983 Volume 31 Issue 9 Pages 3342-3345
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome pyrido-, azepino-, and azocino [3, 4, 5-hi] indolizines were obtained in excellent yields by the intramolecular 1, 3-dipolar addition of pyridinium dicyanomethylides having non-activated acetylenic dipolarophiles in the same molecules.View full abstractDownload PDF (375K) -
Masahito Ochiai, Kenzo Sumi, Eiichi Fujita, Shinichi Tada1983 Volume 31 Issue 9 Pages 3346-3349
Published: September 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSequential addition of lithium salt of carbanion and tributylstannylmethyl iodide (3) to vinyl sulfone 2 afforded β-tributylstannyl sulfones 5, which gave substituted allylsilanes 1 in a regioselective manner by the smooth destannylsulfonation. Allylsilane 8 prepared by Michael type addition of isopropenyllithium to 2 was converted into tagetones (10).View full abstractDownload PDF (364K)