A straightforward synthesis of (-)-phaseolinic acid

Marta Amador; Xavier Ariza; Jordi Garcia; Jordi Ortiz

doi:10.1021/jo048705x

A straightforward synthesis of (-)-phaseolinic acid

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

Authors

Marta Amador¹, Xavier Ariza, Jordi Garcia, Jordi Ortiz

Affiliation

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

PMID: 15527317
DOI: 10.1021/jo048705x

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis*
4-Butyrolactone / chemistry
Basidiomycota / chemistry
Biological Factors / chemical synthesis*
Biological Factors / chemistry
Indicators and Reagents
Molecular Structure
Stereoisomerism

Substances

Biological Factors
Indicators and Reagents
phaseolinic acid
4-Butyrolactone