化学学报 ›› 1988, Vol. 46 ›› Issue (5): 472-477. 上一篇    下一篇

研究论文

不对称羟内酯化合成白三烯A4中间体

王燕芳;李金翠;吴毓林   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1988-05-15

An asymmetric synthesis of leukotriene A4 key intermediate

WANG YANFANG;LI JINCUI;WU YULIN   

  • Published:1988-05-15

为合成白三烯A4的关键中间体, 本文试验了若干7-手性中心-6,5-双键庚酸衍生物的不对称环氧化方法, 发现从D-甘油醛得的顺式烯化合物可选择性地羟内酯化, 游离羟基甲磺酰化后甲醇纳处理可得所需的5S, 6R氧桥, 水解, 过碘酸钠断键后即可顺利得到目标化合物.

关键词: 中间体, 环氧化反应, 酯化, 羧酸酯, 立体选择性, 环氧化物, 环氧化物, 醛, 庚酸 P, 二十碳四烯酸 P

For the preparation of the key synthetic intermediate I of leukotriene A4, some asym. epoxidn. methods for 7-chiral 5-heptenoic acid derivatives have been evaluated. The cis-olefin II prepared from D-gluceraldehyde could be selectively hydroxylactonized. The mesylate of the 6-hydroxy compound III was treated with NaOMe to afford the desired (5S,6R)-epoxide IV. Deprotection of the diol group and cleavage with sodium periodate in one pot gave I.

Key words: INTERMEDIATE, EPOXIDATION REACTION, ESTERIFICATION, CARBOXYLIC ACID ESTER, STEREOSELECTIVITY, EPOXIDE, EPOXIDE, ALDEHYDES, HEPTANOIC ACID P, EICOSATETRAENOIC ACID P

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