Chiral synthesis of the 1-C～6-C and the 11-C～20-C fragment of leukotriene B4 from R-and S-2, 3-O-isopropylidene-glyceraldehyde

Acta Chimica Sinica ›› 1993, Vol. 51 ›› Issue (4): 409-414. Previous Articles Next Articles

Original Articles

利用甘油醛进行白三烯B4中1-C～6-C及11-C～20-C片断的手性合成

王燕芳;李金翠;吴毓林

中国科学院上海有机化学研究所;中国科学院生命化学国家重点实验室

发布日期:1993-04-15

Chiral synthesis of the 1-C～6-C and the 11-C～20-C fragment of leukotriene B4 from R-and S-2, 3-O-isopropylidene-glyceraldehyde

WANG YANFANG;LI JINCUI;WU YULIN

Published:1993-04-15

Abstract

A new synthesis of the 1-C~6-C fragment Et 5(S)-(benzoyloxy)-6-oxo-hexanoate (I) and the 11-C~20-C fragment 2(R)-(tert-butyldiphenylsiloxy)dec-4(z)-enal (II) of LTB4 utilizing D-mannitol and L-ascorbic acid as the chiral pool is described resp. The stereoselective addition reaction of the chiral 2,3-O-isopropylidene-glyceraldehyde with propargyl bromide in presence of zinc powder is a key step.

Key words: VITAMIN C, MANNITOL, STEREOSELECTIVITY, ADDITION REACTION, SYNTHESIS METHODS, LEUKOTRIENE, GLYCERALDEHYDE

CLC Number:

O621

Cite this article

WANG YANFANG;LI JINCUI;WU YULIN. Chiral synthesis of the 1-C～6-C and the 11-C～20-C fragment of leukotriene B4 from R-and S-2, 3-O-isopropylidene-glyceraldehyde[J]. Acta Chimica Sinica, 1993, 51(4): 409-414.

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利用甘油醛进行白三烯B4中1-C～6-C及11-C～20-C片断的手性合成

Chiral synthesis of the 1-C～6-C and the 11-C～20-C fragment of leukotriene B4 from R-and S-2, 3-O-isopropylidene-glyceraldehyde

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