New development of Meyers' methodology:: stereoselective preparation of an axially chiral 5,7-fused bicyclic lactam related to circumdatins/benzomalvins and asperlicins

被引：20

作者：

Penhoat, ML

Bohn, P

Dupas, G

Papamicaël, C

Marsais, F

Levacher, V

机构：

[1] Univ Rouen, Lab Chim Organ Fine & Heterocycl, UMR 6014, IRCOF,CNRS, F-76131 Mont St Aignan, France

[2] INSA Rouen, F-76131 Mont St Aignan, France

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 02期

关键词：

D O I：

10.1016/j.tetasy.2005.12.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective preparation of a new Meyers' bicyclic lactam-bridged biaryl 1, highly structurally related to circumdatins, benzornalvins and asperlicins, is reported. Using the popular Meyers' diastereo selective lactamization, under dehydrating conditions (CH2Cl2/reflux/MgSO4), trans-(aS,R,S)-1 was obtained in a rather modest yield of 25% and an excellent diastereoselectivity > 95%. An alternative procedure making use of the activating agents of carboxylic acid (Mukaiyama reagent and FEP) allowed the lactamization process to take place under milder conditions (CH2Cl2/20 degrees C) affording trans-(aS,R,S)-1 in fairly good yields (50%-85%) and in up to 65% de. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：281 / 286

页数：6

共 38 条

[1] Facile and highly stereoselective synthesis of the tetracyclic erythrinane core [J].