Total Synthesis of (±) Tanikolide

Abstract

Abstract The natural polyketide (±)-tanikolide (1) was prepared in eight steps starting from hex-5-enol, Key steps in this synthesis are a Sharpless dihydroxylation and a Grignard reaction between an alkyl halogenide and a ketone. The lactonization occurred spontaneously during the oxidation of the primary alcohol function to the carboxy group.