Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Volume 39, Issue 12
Displaying 1-8 of 8 articles from this issue
  • Seinosuke OTSUKA, Susumu AKUTAGAWA
    1981 Volume 39 Issue 12 Pages 1138-1150
    Published: December 01, 1981
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Metal-assisted natural product syntheses have been shown and continued to undergo remarkable developments. This account briefly surveys current progress in terpene syntheses based on transition metals. The target products are confined mainly to natural monoterpenes and terpenoids, and the starting materials to isoprene and other abundantly available materials. C-C bond formation reactions, based on oligomerization, telomerization, insertion, and coupling reactions were critically surveyed with respect to their regioselectivity and stereochemistry. Similarly, the introduction, exchange or elimination of a functional group in allylic systems are reviewed. Some functionalized allylic compounds are useful because of their facile allyl transfer (exchange) reactions mediated by palladium. Allylic migrations are notable, especially the enantioselective hydrogen migration of prochiral allylamines. Various other synthetic reactions, including a highly stereospecific epoxidation of olefins, are also described.
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  • Haruo MATSUYAMA
    1981 Volume 39 Issue 12 Pages 1151-1162
    Published: December 01, 1981
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Recent developments related to the total syntheses of spermidine and spermine alkaloids are reviewed. Those alkaloids are kukoamine A 11, maytennine 30, celacinnine 31, celallocinnine 32, celafurine 33, celabenzine 34, dihydroperiphylline 35, (±) -dihydropalustrine 73, 75, lunarine 76, lunaridine 77, codonocarpine 79, and (-) -homaline 93. This article is constructed by following chapters : (i) acyclic spermidine and spermine alkaloids, (ii) macrocyclic spermidine alkaloids, (iii) macrocyclic spermine alkaloids, (iv) observations on biosyntheses, and (v) new synthetic methods of macrocyclic aminolactams.
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  • Yoshinobu ODAIRA, Yoshito TOBE
    1981 Volume 39 Issue 12 Pages 1163-1171
    Published: December 01, 1981
    Released on J-STAGE: January 21, 2010
    JOURNAL FREE ACCESS
    Recent advances in the synthesis of the propellanes are reviewed. This article is divided into two parts, Part 1 concerns the available synthetic methods for a variety of propellanes in which the methods are classfied by the type of reactions ; 1) cycloaddition, 2) condensation, 3) reductive dehalogenation and 4) skeletal rearrangement. Part 2 deals with the synthesis of the target propellanes which involve small ring propellane, 1, 4-bridged Dewar benzene, buttaflane, trispiro- [3, 3, 3] -propellane and modhephene.
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  • Kahei TAKASE, Masafumi YASUNAMI
    1981 Volume 39 Issue 12 Pages 1172-1182
    Published: December 01, 1981
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Azulenes are of interest in their chemical and physical properties as one of the fundamental nonbenzenoid aromatic compounds. The present article provides a summary of a new synthetic method of azulene derivatives by the reaction of 2H-cyclohepta [b] furan-2-ones with enamines developed mainly in the author's laboratory. This method could be applied to the syntheses of azulene derivatives having alkyl, aryl, and functional substituents, and of polycyclic aromatic compounds containing azulene ring.
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  • Aroma Constituents of Turkish Tobacco and the Sex Pheromone of Cigarette Beetle (Lasioderma serricorne F.)
    Tatsuji CHUMAN
    1981 Volume 39 Issue 12 Pages 1183-1199
    Published: December 01, 1981
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The present article involves the studies on aroma constituents of turkish tobacco and the sex pheromone of cigarette beetle, of which the former is considered to be the biologically active substances to human and the both are to the insect.
    A comprehensive investigation of aroma constituents of Turkish tobacco showed the existence of terpenoid acids related to tobacco thunberganoids. The degradation of thunberganoids to these terpenoid acids are considered to be closely related to the formation of the tobacco characteristic aroma.
    In the course of our another studies on the biologically active substances to cigarette beetle, a serious pest of cured tobacco leaves, a sex pheromone, 4, 6-dimethyl-7-hydroxynonan-3-one (serricornin) and other 4, 6-dimethylnonane derivatives as minor components were isolated. The presence of these 4, 6-dimethylnonane derivatives suggests that these pheromone components are derived from the polyketide biosynthesis.
    These biologically active substances were synthesized in practical scale and now the applications of these chemicals as tobacco flavors and the attractants of cigarette beetle are in progress.
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  • Mitsuo MAEDA
    1981 Volume 39 Issue 12 Pages 1200-1209
    Published: December 01, 1981
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Dye laser is a very useful device for some chemical applications such as spectroscopy, laserinduced chemical reaction, and picosecond flash-photolysis, because it generates a coherent radiation with a very wide tunable range from 311 nm to 1285 nm. More than 500 kinds of fluorescent organic chemicals show laser action under intense excitation by a flashlamp or other lasers. In this review, a fundamental principle and characteristics of dye lasers are described. Then, useful and efficient chemicals used for dye lasers are reviewed. Most important classes of dye laser materials are polymethine dyes, xanthene dyes, oxazine dyes, coumarin derivatives, stilbene derivatives and p-origophenylenes.
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  • Akio TOSHIMITSU, Sakae UEMURA
    1981 Volume 39 Issue 12 Pages 1210-1221
    Published: December 01, 1981
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Oxyselenation reactions, which involve an electrophilic attack of organoselenium group on olefin and acetylene followed by a nucleophilic attack of oxygen atom of alcohol, carboxylic acid, water etc, are reviewed, especially focusing on the recent application to organic synthesis. The term of solvoselenation is introduced for the first time as a more general name for the oxyselenation type reaction in various solvents such as ROH, RCO2 H, RCN etc.
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  • Effective Catalysts for Double Bond Migration Reaction
    Hiroharu SUZUKI, Yoshihiko MORO-OKA
    1981 Volume 39 Issue 12 Pages 1222-1227
    Published: December 01, 1981
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Ruthenium hydride complexes, which can be easily prepared from ruthenium trichloride in high yields, are readily available for the migration reaction of carbon- carbon unsaturated bonds under neutral conditions. The functional groups, being capable of (n-π) or (π-π) conjugation with the migrated carbon-carbon unsaturation, control regioselectively the double bond migration. Utility of the double bond migration reactions catalyzed by ruthenium hydride complexes is demonstrated by several examples.
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