Total Synthesis of (+)-Goniodenin

Abstract

Goniodenin is a lipophilic polyketide originating from plant sources and which possesses a potent cytotoxic activity against cancer cell lines. The first total synthesis of (+)-goniodenin has been achieved in 23 steps from (R)-glycidol. The synthetic sequence featured a cross metathesis for the formation of the C-C bond and installation of the terminal γ-butenolactone ring unit by the alkylation of α-phenylthio-γ-butyrolactone with the corresponding C-O-triflate. The stereogenic center at C carbon was created by Hiyama-Fujita reduction of the corresponding ketone with high diastereoselectivity.