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化学学报
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化学学报 ›› 1990, Vol. 48 ›› Issue (10): 1024-1029. 上一篇    下一篇

研究论文

白三烯B4中11-C-20-C片断的合成和硅醚保护基团的移位

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:1990-10-15

Synthesis of 11-C-20-C segment of leukotriene B4 and migration of silyl protecting group

WANG YANFANG;LI JINCUI;WU YULIN   

  • Published:1990-10-15

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本文报道由抗坏血酸为手性源合成白三烯B4中11-C-20-C片断2R-羟基-癸-4(Z)-烯醛衍生物的新路线。在此合成过程中也发现Wittig反应时硅醚保护基由仲羟基向邻位伯羟基的部分以至完全移位的状况。

关键词: 醚, 维蒂希反应, 移位, 醛, 硅烷, 癸烯 P, 白三烯, 保护基

A new synthesis of 11-C-20-C segment of leukotriene B4, 2(R)-hydroxydec-4(Z)-enal derivatives I (R = SiPh2CMe3, SiMe2CMe3, CPh3) using ascorbic acid as chiron is described. A partial or full migration of silyl protecting group from a secondary hydroxy group to a vicinal primary one is discovered in the Wittig reaction of hemiacetals II (R1 = SiPh2CMe3, SiMe2CMe3) with Me(CH2)5P+Ph3Br-.

Key words: ETHER, WITTIG REACTION, SHIFTS, ALDEHYDES, SILANE, DECENE P, LEUKOTRIENE, PROTECTIVE GROUP

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