Total Synthesis of (−)-Reveromycin A

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 hemis...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2004-08, Vol.6 (17), p.3001-3004
Main Authors: El Sous, Mariana, Ganame, Danny, Tregloan, Peter A, Rizzacasa, Mark A
Format: Article
Language:English
Subjects:
Combinatorial Chemistry Techniques
Indicators and Reagents
Molecular Structure
Pyrans - chemical synthesis
Spiro Compounds - chemical synthesis
Stereoisomerism
Streptomyces - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048811l