Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 50, Issue 1
Displaying 1-8 of 8 articles from this issue
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  • [title in Japanese]
    1992Volume 50Issue 1 Pages 2-13
    Published: January 01, 1992
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.2
    JOURNAL FREE ACCESS
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  • Optical Resolution of Organic Compounds by Means of Crystallization and Their Applications
    Hiroyuki NOHIRA
    1992Volume 50Issue 1 Pages 14-23
    Published: January 01, 1992
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.14
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    Some new methods and practical strategies for the efficient resolution of a wide variety of organic componds by means of such crystallization procedures as preferential crystallization, diastereomeric salt formation and their combination are described. Utilizing the organic compounds with high optical purities thus obtained, application study in the following field has been performed;1) verification of the Brewster's theory of optical activity, 2) syntheses of pharmaceutical, agricultural and perfuming chemicals, 3) preparation of optical purity determining agents, 4) preparation of atropisomeric bis (triarylphosphine) as a catalyst for asymmetric hydrogenation, 5) syntheses of ferroelectric liquid crystals. In this article, an outline of our investigation in the above mentioned fields is also described.
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  • Preparation and Modification of Nucleic Acids by Condensation in Aqueous Solution
    Hiroaki SAWAI, Kazuo SHINOZUKA
    1992Volume 50Issue 1 Pages 24-34
    Published: January 01, 1992
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.24
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    This review article describes preparation and modification of oligonucleotides by condensation in aqueous solution. Nucleotides and oligonucleotides are generally soluble in water, but not in organic solvents. Reactions in aqueous solution are therefore indispensable. Condensation in aqueous media is thermodynamically unfavorable. Several methods have been devised to overcome this problem. Large amount of water soluble condensing agents such as EDC or cyanogen bromide are employed for the condensation of oligonucleotides. Use of imidazole-activated nucleotides is an another approach for the preparation and the modification of oligonucleotides. The control of pH of the reaction media is necessary to accomplish the efficient and regioselective condensation. Metal ions or polynucleotide template, wihch organize the substrate nucleotides by complex formation promote the target condensation.
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  • Recent Developments in the Preparation of Cyclic Silicon Compounds Containing Heteroatoms (N, P, S)
    Akihito SAKAKIBARA, Wataru ANDO
    1992Volume 50Issue 1 Pages 35-47
    Published: January 01, 1992
    Released on J-STAGE: January 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.35
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    Cyclic silicon compounds containing heteroatoms (N, P, S), as cyclosilazanes, cyclosilaphosphanes, and cyclosilthianes have been energetically investigated as synthetic targets in a field of silicon chemistry. In the interest of chemical industry, cyclosilazanes as well as cyclosiloxanes are useful in the preparation of linear polymer. The importance of polysilazanes as preceramic materials is well-konwn. But the possibility of cyclosilaphosphanes and cyclosilthianes as the industrial materials have not been discussed in detail.
    In this review, the recent developments in the field of cyclic silicon compounds containing heteroatoms (N, P, S) are summarized from the above point of view.
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  • Synthesis of Organosilicon Compounds as Synthetic Equivalents of Unstable Active Chemical Species and Their Applications to Highly Selective Synthesis of Heterocycles
    Yoshinori TOMINAGA, Makoto HOJO, Akira HOSOMI
    1992Volume 50Issue 1 Pages 48-60
    Published: January 01, 1992
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.48
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    Various organosilicon compounds act as synthetic equivalents of unstable active chemical species, especially novel 1, 3-dipolar reagents such as azomethine ylides, thiocarbonyl ylides and related reagents, are designed and synthesized. These compounds activated by a Lewis acid or fluoride ion react with a variety of dipolarophiles and hetero-dipolarophiles in highly regio- and stereospecific mode. It has been found that this methodology can be extended to the design and preparations of tailor-made 1, 3-dipolar reagents. The highly selective synthesis of heterocycles are described.
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  • Total Synthesis of Neooxazolomycin
    Kuniaki KAWAMURA, R.J. DeVita, A.S. Kende
    1992Volume 50Issue 1 Pages 61-70
    Published: January 01, 1992
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.61
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    The first enantioselective total synthesis of neooxazolomycin (1), structurally unique antitumor agent isolated from streptomyces sp., is described. The key steps of the synthesis involve the following newly developed synthetic methods : i) the novel dianion cyclocondensation reaction of amide-malonate 3 with ester 36 followed by stereoselective lactonization to give the fused bicyclic lactam-lactone terminus, ii) the four carbon homologation of aldehyde 41 to E, E-dienamide 45 via vinyliodide 43 by means of the mild Pd-catalyzed coupling with the vinylstannane 13, (iii) the diastereoselective Reformatsky type aldol reaction of Z-enal 48 with the tin (II) enolate derived from chiral oxazolidinone 15 to give R, S-oxazinedione 51. Utilizing the above key reactions and further manipulations afforded the right half amine 71 and the left half acid 68 in proper chiral form. Finally, the amide formation of them followed by deprotection gave the synthetic neooxazolomycin (1).
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  • Diazodiphenylmethane, C13H10N2
    Yoshihiko HIRAYAMA, Yukitomo KOUNO
    1992Volume 50Issue 1 Pages 71-73
    Published: January 01, 1992
    Released on J-STAGE: January 28, 2010
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.71
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    [in Japanese]
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  • [title in Japanese]
    [in Japanese], [in Japanese]
    1992Volume 50Issue 1 Pages 74
    Published: January 01, 1992
    Released on J-STAGE: November 16, 2009
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.50.74
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