A convenient stereoselective synthesis of castasterone and its analogues using arsenic ylides

被引：10
作者：
Werner, F
Parmentier, G
Luu, B
Dinan, L
机构：
[1] UNIV STRASBOURG 1, CNRS, LAB CHIM ORGAN SUBST NAT, F-67084 STRASBOURG, FRANCE
[2] UNIV EXETER, DEPT BIOL SCI, EXETER EX4 4QG, DEVON, ENGLAND
来源：
TETRAHEDRON | 1996年 / 52卷 / 15期
关键词：
D O I：
10.1016/0040-4020(96)00186-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(2 alpha,3 alpha,22S)-Trihydroxy-5 alpha-cholestan-6-one 3 and (2 alpha,3 alpha,22R)-trihydroxy-5 alpha-cholestan-6-one 4 have been synthesized with high stereoselectivity. The key step is the coupling of the aldehyde 5 with an arsenic ylide, followed by an in situ DIBAH reduction. A second arsenic ylide was used to prepare the key allylic alcohol intermediate 15, which allows the synthesis of castasterone 2. Copyright (C) 1996 Elsevier Science Ltd
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页码：5525 / 5532
页数：8
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