（-）-菜豆酸的直接合成。

A straightforward synthesis of (-)-phaseolinic acid.

作者信息

Amador Marta, Ariza Xavier, Garcia Jordi, Ortiz Jordi

机构信息

Departament de Química Orgànica, Universitat de Barcelona, C/ Martí i Franquès 1-11, E-08028 Barcelona, Catalonia, Spain.

出版信息

J Org Chem. 2004 Nov 12;69(23):8172-5. doi: 10.1021/jo048705x.

DOI:10.1021/jo048705x

PMID:15527317

Abstract

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.

摘要

公开了一种从市售的(S)-辛-1-炔-3-醇出发合成(-)-菜豆酸的简洁方法。关键步骤是通过关环复分解反应制备一个C(2)对称的烯丙基二醇，以及利用爱尔兰-克莱森重排反应将其不对称化为γ-丁内酯。左旋天然产物的2S,3S,4S构型已得到确证。