Natural product synthesis based on new acyclic stereocontrol. Stereoselective total syntheses of zincophorin, the lonophore antibiotic, and scytophycin C, an antitumor marine macrolide

Abstract

There have been found in nature a variety of polypropionate-derived natural products exhibiting potent pharmacological properties as well as biological activities, as exemplified by various antibiotics that have played clinically important roles. In order to synthesize these natural products stereoselectively and to open a completely chemical avenue to these compounds and their analogues, stereospecific construction methodologies for acyclic organic molecules bearing contiguous asymmetric carbon atoms are of critical importance. In this article, the development of new types of acyclic stereocontrol and their application to natural product synthesis are described, in which stereoselective total syntheses of zincophorin, the ionophore antibiotic, and a potent antitumor marine natural product, scytophycin C, a 22-membered macrolide with structural and stereochemical complexity, are discussed.