Synthetic studies on Terpenoid lactones

Abstract

A novel stereoselective route has been developed to a vernolepin intermediate in nine steps from 2-phenylthiocyclopentenone. During this research, a regiospecific method for the alkylation of the Δ5,6 - tetrahydroindanone system has been achieved. In addition, the synthetic route demonstrates a means of differentiating between two carboxylic acid functions via a selective lactonisation. The first total ynthesis of boonein has also been completed, in 3% yield from cyclopentadiene. This route uses a chlorine atom to direct the stereo- and regiochemical outcome of most of these reaction.