Total Synthesis of
(-)-Reveromycin A via a Hetero-Diels-Alder Approach

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

doi:10.1055/s-0030-1258308

FEATUREARTICLE

Total Synthesis of (-)-Reveromycin A via a Hetero-Diels-Alder Approach

Mariana El Sous, Danny Ganame, Peter Tregloan, Mark A. Rizzacasa*
School of Chemistry, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, 3010 Victoria, Australia
Fax: +61(3)93478396; e-Mail: masr@unimelb.edu.au;

Abstract

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Abstract

The asymmetric total synthesis of (-)-reveromycin A is described which utilizes a Lewis acid catalyzed inverse electron demand hetero-Diels-Alder reaction followed by hydroboration/oxidation to afford the labile [6,6]-spiroketal core in a highly stereoselective manner. An asymmetric syn-aldol reaction installed the stereochemistry at C4-C5 whilst a Stille cross coupling was utilized to form the C21-C22 bond. The C18 hemisuccinate was formed by high pressure acylation reaction and a final Wittig extension followed by global deprotection with tetrabutylammonium fluoride gave (-)-reveromycin A.

Key words

reveromycin - [6,6]-spiroketal - hetero-Diels-Alder - high-pressure acylation - Stille coupling

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