Vic-Tricarbonyl Compounds: Synthesis of (±)-9-epi-Wailupemycin A

Dedicated to Prof. R. W. Hoffmann on the occasion of his 80^th birthday

Abstract

A synthesis of the 9-epimer of the marine natural product wailupemycin A is reported. The key reaction sequence consists of a diastereoselective enamine addition to a tricarbonyl monohydrate, the formation of an enol silyl acetal, and finally the stereocontrolled addition of the α-pyrone substructure.

Key words

vicinal tricarbonyl compound - enamine - α-pyrone - natural products - stereoselective synthesis

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