Ab initio and semiempirical corroboration of the observed stereoselectivity in the transannular Diels-Alder reaction leading to steroids

被引：8

作者：

Couturier, M

Dory, YL

Fortin, D

Rouillard, A

Deslongchamps, P ^{[1
]}

机构：

[1] Univ Sherbrooke, Inst Pharmacol Sherbrooke, Dept Chim, Synth Organ Lab, Sherbrooke, PQ J1H 5N4, Canada

[2] Univ Sherbrooke, Inst Pharmacol Sherbrooke, Dept Chim, Lab Modelisat Mol, Sherbrooke, PQ J1H 5N4, Canada

来源：

TETRAHEDRON | 1998年 / 54卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(98)00600-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various 14-membered macrocyclic trienes underwent transannular Diels-Alder reactions to yield tetracyclic structures that are streoisomers of steroids. Due to the complexity of the effects at work during these reactions, a thorough molecular modeling study was carried out. Thus, some molecular mechanics, semiempirical and db initio methods were compared and the results were finally used to rationalize the experimental results. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：10089 / 10110

页数：22

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