Total synthesis of zincophorin and its methyl ester

Magali Defosseux; Nicolas Blanchard; Christophe Meyer; Janine Cossy

doi:10.1021/jo0496042

Total synthesis of zincophorin and its methyl ester

J Org Chem. 2004 Jul 9;69(14):4626-47. doi: 10.1021/jo0496042.

Authors

Magali Defosseux¹, Nicolas Blanchard, Christophe Meyer, Janine Cossy

Affiliation

¹ Laboratoire de Chimie Organique, asocié au CNRS, ESPCI, 10 rue Vauquelin 75231 Paris Cedex 05 - France.

PMID: 15230584
DOI: 10.1021/jo0496042

Abstract

A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Carboxylic Acids / chemical synthesis*
Combinatorial Chemistry Techniques*
Esters
Indicators and Reagents
Molecular Structure
Propionates
Stereoisomerism

Substances

Anti-Bacterial Agents
Carboxylic Acids
Esters
Indicators and Reagents
Propionates
zincophorin methyl ester
zincophorin