Total Synthesis of (+)-Goniodenin.

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-8-C-9 bond and installation of the terminal gamma-butenolactone ring unit by the allcylation of alpha-phenylthio-gamma-butyrolactone with the corresponding C-3-O-triflate. The stereogenic center at C-18 carbon was created by Hiyama Fujita reduction of the corresponding ketone with high diastereoselectivity.