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

We devised an efficient synthetic method to prepare a novel apoptosis inducer, F-3-2-5 by using octanol-accelerated Baylis-Hillman reaction as the key step. Particularly, as the reaction conditions were confirmed to provide the title compound in large quantity, this method opens a door for extensive structure-activity relationship study as well as preclinical study of the title compound. F-3-2-5 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. 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