Journal of Synthetic Organic Chemistry, Japan

Studies towards Stereoselective Synthesis of 1, 3-syn-and anti-Polyols. Synthesis of Natural Products Containing 1, 3-Polyol System

Tadashi NAKATA, Takeshi OISHI

1986Volume 44Issue 4 Pages 298-308
Published: April 01, 1986
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.298

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Highly stereocontrolled methods for the syntheses of 1, 3-syn-and anti-polyols have been developed based on the stereoselective reduction of six-membered β-keto acetal and successive acetalthioacetal interchange. These methods have been successfully applied to the synthesis of (1 R, 3 R, 5 S) -1, 3-dimethyl-2, 9-dioxabicyclo [3. 3. 1] nonane, synthesis and the absolute configuration determination of (-) -tarconunthuslactone, total synthesis of (+) -pederin, and formal total synthesis of (+) -aplasmomycin.

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Double Asymmetric Synthesis

a New Strategy for Stereochemical Control in Organic Synthesis (Part 1)

Tsuneo SATO, Atsushi ABIKO, Satoru MASAMUNE

1986Volume 44Issue 4 Pages 309-325
Published: April 01, 1986
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.309

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This account examines double asymmetric induction from theoretical and practical viewpoints. In the context of four major organic reactions-the aldol, Diels-Alder, catalytic hydrogenation, and epoxidation-it is shown that a double asymmetric induction can be analyzed in terms of the single asymmetric reactions of each of the two chiral reactants. A rule which qualitatively relates the results of these single asymmetric reactions with the outcome of the double asymmetric reaction is proposed. A powerful new strategy based on this rule for the predictable creation of new chiral centers is discussed and the use of this strategy for the synthesis of sugars and macrolides is presented.

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A Synthetic Study of Alkaloids Containing Piperidine Ring

Mitsutaka NATSUME

1986Volume 44Issue 4 Pages 326-339
Published: April 01, 1986
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.326

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Variously substituted 1-alkoxycarbonyl-1, 2-dihydropyridine compounds derived from corresponding alkylpyridines were utilized as building blocks for synthesizing alkaloids containing a piperidine ring. These dihydro derivatives were submitted to the sensitized photooxygenation, followed by a novel ring-opening reaction of the endoperoxides formed here, with nucleophiles such as trimethylsilyl enol ethers or indole in the presence of stannous chloride. 1-Alkoxycarbonyl-2, 6-dialkyl-1, 2, 3, 6-tetrahydro-3-pyridinols and 1-benzyloxycarbonyl-6- (3-indolyl) -4, or 5- (2-methyl-1, 3-dioxan-2-yl) -1, 2, 3, 6-tetrahydro-3-pyridinol were obtained as stereochemically definite compounds and these were applied to the total synthesis of Sedum alkaloids, sedacryptine and sedinine, a horsetail alkaloid, palustrine, and indole alkaloids, epiuleine and vindorosine, as important starting materials.

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Recent Topics in Synthetic Studies on Fragrance and Flavor Compounds

Yoshikazu TAKAGI, Kunio KOGAMI

1986Volume 44Issue 4 Pages 340-353
Published: April 01, 1986
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.340

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The elucidation of the chemical structure on natural aromatic components being advanced, new excellent synthetic methods for them have been developed. Various novel fragrance and flavor compounds have been produced one after another.
Recent topics in the interesting syntheses on main components of natural essential oils, important constituents of animal perfumes and key substances in natural food flavors are reviewed with 64 references.

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The Description of Organic Reactions

Shinsaku FUJITA

1986Volume 44Issue 4 Pages 354-364
Published: April 01, 1986
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.354

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I discuss various methods of describing organic reactions in order to construct such an integrated system as will support both retrieval and synthetic design : keywords, codes (such as Theilheimer' s, Cohen' s, GREMAS, Hendrickson' s and Litter' s one), graphical expressions by Roberts and Hendrickson, methods based on connection tables of substrates and products (Corey, Matsuura, and Dubois), and matrix representations (Ugi and Arens). I reveal “Structure-Reaction type” paradigm which has been hidden in these conventional methods.

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Recent Development of Automatic Synthesizing System

Nucleic Acids Automatic Synthesizing System

Yasuyoshi CHINO, Ryoji SATO

1986Volume 44Issue 4 Pages 365-374
Published: April 01, 1986
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.365

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Recent development of the automatic DNA-synthesizer using the phosphite-triester method for the oligodeoxyribonucleotide synthesis was reviewed with the outline of the basic strategies.
Some of the practical key points in designing an automatic synthesizing system were also commented.

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Glyoxal (CHO/CHO)

Kazuhisa NAKAJIMA

1986Volume 44Issue 4 Pages 375
Published: April 01, 1986
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.375

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[title in Japanese]

[in Japanese], [in Japanese], [in Japanese]

1986Volume 44Issue 4 Pages 376
Published: April 01, 1986
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.44.376

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