A straightforward synthesis of (-)-phaseolinic acid

被引：45
|
作者：
Amador, M [1 ]
Ariza, X [1 ]
Garcia, J [1 ]
Ortiz, J [1 ]
机构：
[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 23期
关键词：
D O I：
10.1021/jo048705x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise approach to (-)-phaseolinic acid starting from commercially available (S)-oct-1-yn-3-ol is disclosed. The key steps are a ring-closing metathesis reaction to prepare a C-2-symmetrical allylic diol and its desymmetrization to a gamma-butyrolactone by using an Ireland-Claisen rearrangement. The 2S,3S,4S configuration of the levogyre natural product has been confirmed.
引用
收藏
页码：8172 / 8175
页数：4
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