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

Acta Chimica Sinica ›› 1990, Vol. 48 ›› Issue (10): 1024-1029. Previous Articles Next Articles

Original Articles

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

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

Abstract

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

CLC Number:

O621

Cite this article

WANG YANFANG;LI JINCUI;WU YULIN. Synthesis of 11-C-20-C segment of leukotriene B4 and migration of silyl protecting group[J]. Acta Chimica Sinica, 1990, 48(10): 1024-1029.

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白三烯B4中11-C-20-C片断的合成和硅醚保护基团的移位

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

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