Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin

被引：80

作者：

Andrey, O ^{[1
]}

Vidonne, A ^{[1
]}

Alexakis, A ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 43期

关键词：

D O I：

10.1016/j.tetlet.2003.09.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric Michael addition of propionaldehyde to(2E)-(3-nitro-but-2-enyloxymethyl)-benzene 8, catalyzed by the chiral diamine (S,S)-N-iPr-2,2'-bipyrrolidine, afforded, with 93% ee, a precursor 9 of (-)-botryodiplodin. The nitro functionality of 9 was converted to a ketone via a Nef reaction to give, after a few steps, the enantiomerically enriched (-)-botryodiplodin. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7901 / 7904

页数：4

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