Total synthesis of polyrhacitides A and B by use of an iterative strategy for the stereoselective synthesis of 1,3-polyol arrays

Helge Menz; Stefan F Kirsch

doi:10.1021/ol902135v

Total synthesis of polyrhacitides A and B by use of an iterative strategy for the stereoselective synthesis of 1,3-polyol arrays

Org Lett. 2009 Dec 17;11(24):5634-7. doi: 10.1021/ol902135v.

Authors

Helge Menz¹, Stefan F Kirsch

Affiliation

¹ Department Chemie and Catalysis Research Center, Technische Universitat Munchen, Lichtenbergstr. 4, 85747 Garching, Germany.

PMID: 19919037
DOI: 10.1021/ol902135v

Abstract

The first total syntheses of polyrhacitides A and B, secondary metabolites from Chinese medicinal ants, were accomplished via an iterative approach to the 1,3-polyol motif. For the construction of all stereogenic centers, the catalytic asymmetric Overman esterification was utilized.

Publication types

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

MeSH terms

Animals
Ants / chemistry
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Catalysis
Esterification
Humans
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure
Polymers / chemical synthesis*
Polymers / chemistry
Stereoisomerism

Substances

Bridged Bicyclo Compounds, Heterocyclic
Lactones
Polymers
polyol
polyrhacitide A
polyrhacitide B