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Synthesis 2010(23): 3954-3966  
DOI: 10.1055/s-0030-1258308
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

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;
Further Information

Publication History

Received 30 September 2010
Publication Date:
21 October 2010 (online)

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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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