Total synthesis of (-)-reveromycin a

Mariana El Sous; Danny Ganame; Peter A Tregloan; Mark A Rizzacasa

doi:10.1021/ol048811l

Total synthesis of (-)-reveromycin a

Org Lett. 2004 Aug 19;6(17):3001-4. doi: 10.1021/ol048811l.

Authors

Mariana El Sous¹, Danny Ganame, Peter A Tregloan, Mark A Rizzacasa

Affiliation

¹ School of Chemistry, The University of Melbourne, Victoria 3010, Australia.

PMID: 15330668
DOI: 10.1021/ol048811l

Abstract

The asymmetric total synthesis of (-)-reveromycin A is described. The key steps involved a Lewis acid catalyzed inverse electron demand hetero-Diels-Alder reaction followed by hydroboration/oxidation to afford the spiroketal core 4 in a highly stereoselective manner and introduction of the C18 hemisuccinate by high-pressure acylation.

Publication types

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

MeSH terms

Combinatorial Chemistry Techniques*
Indicators and Reagents
Molecular Structure
Pyrans / chemical synthesis*
Spiro Compounds / chemical synthesis*
Stereoisomerism
Streptomyces / chemistry

Substances

Indicators and Reagents
Pyrans
Spiro Compounds
reveromycin B
reveromycin A