TOTAL SYNTHESIS OF LEUKOTRIENE-B(4)

被引:30
作者
KERDESKY, FAJ
SCHMIDT, SP
BROOKS, DW
机构
[1] Process Research and Immunoscience, Pharmaceutical Products Division, Abbott Laboratories, Illinois 60064, Abbott Park
关键词
D O I
10.1021/jo00065a012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, efficient, and stereocontrolled total synthesis of leukotriene B4 (1) has been developed. The convergent route employs a stereospecific Horner-Wadsworth-Emmons coupling of propargylic phosphonate 2 and aldehyde 3 to provide the essential carbon framework in 77% yield. The requisite phosphonate 2 containing the C1-C8 fragment was readily prepared in 47% yield from methyl 4-(chloroformyl)butyrate via an enantioselective reduction of alcohol 4 while the chiral aldehyde 3 which comprises the C9-C20 skeleton of the eicosanoid was synthesized in 52% yield from optically active (2R)-(-)-glycidyl 4-nitrobenzoate.
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页码:3516 / 3520
页数:5
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