A short multigram asymmetric synthesis of prostanoid scaffolds

被引：23

作者：

Depré, D

Chen, LY

Ghosez, L

机构：

[1] Univ Louvain, Dept Chem, B-1348 Louvain, Belgium

[2] ENSCPB, IECB, European Inst Chem & Biol, F-33607 Pessac, France

来源：

TETRAHEDRON | 2003年 / 59卷 / 35期

关键词：

2+2] cycloadditions; keterummium salts; allylmetallation; cyclobutanones; bicyclic lactones;

D O I：

10.1016/S0040-4020(03)00920-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from gamma-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantionneric purities. (C) 2003 Elsevier Ltd. All rights reserved.

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收藏

页码：6797 / 6812

页数：16

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