Enantioselective synthesis of the ester side chain of homoharringtonine

被引：27
|
作者：
Keller, L [1 ]
Dumas, F [1 ]
d'Angelo, J [1 ]
机构：
[1] Univ Paris Sud, Ctr Etud Pharmaceut, CNRS, Unite Associee, F-92296 Chatenay Malabry, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 13期
关键词：
asymmetric synthesis; Michael additions; ozonolysis; protecting groups; total synthesis;
D O I：
10.1002/ejoc.200300111
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Details of the synthesis of the methyl ester of the side chain of homoharringtonine, a natural product with antileukemic properties, are reported below. The key tactical element involved a Michael addition between the known chiral imine 4 and 2-acetoxyacrylonitrile (5), furnishing the adduct (2R,1'R)-6 with a high degree of regio- and stereoselectivity. This adduct was then converted into the target compound (R)-2 by a linear sequence of ten chemical operations, in 6.0% overall yield. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码：2488 / 2497
页数：10
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