AN INVESTIGATION INTO THE TOTAL SYNTHESIS OF CLEROCIDIN - STEREOSELECTIVE SYNTHESIS OF A CLERODANE INTERMEDIATE

A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesi zed by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions w ere developed to introduce the axial methyl group at the C-8 position. A palladium-mediated carbonylation reaction was employed to generate the key alpha,beta-unsaturated dialdehyde. (C) 1998 Elsevier Science L td. All rights reserved.