An Efficient Synthesis of an Apoptosis Inducer, F-3-2-5 by Using Octanol-Accelerated Baylis-Hillman Reaction

Abstract

F-3-2-5 (Fig. 1) is a novel apoptosis inducer which was recently isolated from Streptomyces sp., of which potent anticancer activity warrants further preclinical investigation as well as extensive structure-activity relationship study. 1 Thus, there has been an urgent need to devise an efficient synthetic method of F-3-2-5 which has a synthetically challenging trisubstituted α,β-unsaturated ketone moiety as an integral part. Herein, we report an efficient synthesis of the title compound by using Baylis-Hillman reaction as the key step. A synthetic plan for the title compound is shown in Figure 2. The Baylis-Hillman reaction 2a,2b of methyl vinyl ketone