Collect. Czech. Chem. Commun. 2009, 74, 887-900
Published online 2009-05-14 09:43:29

Total synthesis of the potent antifungal agents bengazole C and E

Álvaro Enríquez-García and Steven V. Ley*

Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK


The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

Keywords: Antifungal agents; Cycloaddition; Oxazoles; Natural products; Total synthesis; Bengazoles; Marine compounds.

References: 18 live references.