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.
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