Total synthesis of a curvularin isomer

Abstract

This paper describes a total synthesis of a biogenetically possible, hitherto unknown macrolide 4. Starting with 3,5-dimethoxybenzaldehyde, ketone 5a was generated in five steps. Alkylation of this compound by bromopentene followed by decarboxylation yielded pentenyl ketone 6. Oxymercuration–demercuration followed by dehydration gave cyclic enol ether 8. Oxidation with m-chloroperbenzoic acid led to the macrolide 4.