Stereoselective synthesis of (-)-cephalotaxine and C-7 alkylated analogues

被引：64

作者：

Planas, L ^{[1
]}

Pérard-Viret, J ^{[1
]}

Royer, J ^{[1
]}

机构：

[1] Univ Paris 05, CNRS, Fac Sci Pharmaceut & Biol, UMR 8638, F-75270 Paris 06, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 09期

关键词：

D O I：

10.1021/jo049884l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total asymmetric synthesis of (-)-cephalotaxine is reported. The chemistry of alpha,beta-unsaturated gamma-lactams was used to access the 1-azaspiro[4.4]nonane skeleton in enantiomerically pure form via a stereocontrolled semipinacolic rearrangement of an alpha-hydroxyiminium ion. This Spiro compound was transformed into (-)-cephalotaxine without any racemization or epimerization by following the racemic synthesis reported by Kuehne. We thus performed a total synthesis of (-)-cephalotaxine in 98.7% ee with an overall yield of 9.8% over a 16 steps sequence. This synthetic process was adaptable to the access of some alkylated analogues.

引用

页码：3087 / 3092

页数：6

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