Journal article
Total synthesis of (-)-reveromycin A via a hetero-Diels-Alder approach
M El Sous, D Ganame, P Tregloan, MA Rizzacasa
Synthesis | Published : 2010
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. © Georg Thieme Verlag Stuttgart - New York.
Grants
Funding Acknowledgements
We are indebted to Dr. Hiroyuki Osada (RIKEN Institute, Japan) for an authentic sample of reveromycin A (1) as well as copies of the NMR spectra. We also thank Professor Rob Capon (University of Queensland) for the HPLC comparisons. This work was financially supported by the Australian Research Council.