Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies

Dieter Muri; Erick M Carreira

doi:10.1021/jo901817b

Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies

J Org Chem. 2009 Nov 20;74(22):8695-712. doi: 10.1021/jo901817b.

Authors

Dieter Muri¹, Erick M Carreira

Affiliation

¹ Laboratorium für Organische Chemie, ETH Hönggerberg, Wolfgang Pauli Strasse 10, CH-8093 Zürich, Switzerland.

PMID: 19839571
DOI: 10.1021/jo901817b

Abstract

An expeditious synthesis of erythronolide A is documented. Key steps of the approach include two magnesium-mediated nitrile oxide cycloadditions, a chelation-controlled Grignard reaction, and a Sharpless asymmetric dihydroxylation.

Publication types

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

MeSH terms

Cyclization
Erythromycin / analogs & derivatives*
Erythromycin / chemical synthesis
Erythromycin / chemistry
Molecular Conformation
Nitriles / chemistry*
Oxides / chemistry*
Stereoisomerism

Substances

Nitriles
Oxides
erythronolide A
Erythromycin