Chiral syntheses of dihydroxyamino acid moieties of AI-77-B and calyculins from D-glucosamine

被引:0
|
作者
Shinozaki, K [1 ]
Mizuno, K [1 ]
Wakamatsu, H [1 ]
Masaki, Y [1 ]
机构
[1] GIFU PHARMACEUT UNIV, GIFU 502, JAPAN
关键词
D-glucosamine; chiral pool; (2S,3S,4S)-2,3-dihydroxy-4-aminohexanedioic acid; (2S,3S,4S)-2,3-dihydroxy-4-dimethylamino-5-methoxypentanoic acid; synthesis;
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Manipulation of cis (4S,5S)-4,5-disubstituted 2-oxazolidinones (4, 5), derived easily from D-glucosamine (1) as a chiral pool, including degradation of the C6-carbon and/or one-carbon homologation at the C1-position allowed chiral syntheses of (2S,3S)-dihydroxy-(4S)-amino acid moieties (6-8), which are important structural components of a gastroprotective substance, AI-77-B, and a group of antitumor substances, calyculins.
引用
收藏
页码:1823 / 1830
页数:8
相关论文
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  • [1] CHIRAL SYNTHESIS OF THE HYDROXY AMINO-ACID MOIETY OF AI-77-B
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    MONDON, M
    TETRAHEDRON LETTERS, 1989, 30 (47) : 6503 - 6506
  • [2] EFFICIENT TOTAL SYNTHESIS OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77
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    HARA, O
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    KOHNO, Y
    SHIOIRI, T
    TETRAHEDRON, 1991, 47 (40) : 8635 - 8652
  • [3] STEREOSELECTIVE SYNTHESIS OF THE HYDROXY AMINO-ACID MOIETY OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77
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    TETRAHEDRON LETTERS, 1988, 29 (48) : 6331 - 6334
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