A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction

被引：28

作者：

Cabanal-Duvillard, I

Berrien, JF

Ghosez, L

Husson, HP

Royer, J

机构：

[1] Univ Paris 05, Fac Pharm, CNRS, Chim Therapeut Lab, F-75270 Paris 06, France

[2] Univ Paris 05, Fac Pharm, UMR 8638, F-75270 Paris, France

[3] Univ Catholique Louvain, Lab Chim Organ Synth, B-1348 Louvain, Belgium

[4] Univ Paris 11, Fac Pharm, UPRESA Biocis 8076, F-92296 Chatenay Malabry, France

[5] YNSCPB, IECB, F-33402 Talence, France

来源：

TETRAHEDRON | 2000年 / 56卷 / 23期

关键词：

(-)-epibatidine; asymmetric synthesis; acynitroso compounds; hetero Diels-Alder cycloaddition;

D O I：

10.1016/S0040-4020(00)00284-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal asymmetric synthesis of (-)-epibatidine is reported. The key step of the synthesis is a regio- and diastereoselective cycloaddition of silyloxycyclohexadiene with the acylnitroso dienophile derived from (+)-camphorsultam. The resulting cycloadduct was readily transformed into the N-protected-7-azabicyclo[2.2.1]heptan-2-one derivative which has previously been transformed into (-)-epibatidine. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3763 / 3769

页数：7

共 43 条

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