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

被引：81
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
收藏
页码：7901 / 7904
页数：4
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