Total Synthesis of the Anticancer Marine Natural Product Mycalol

Abstract

This communication describes a synthetic study of the originally proposed structure of mycalol (1) and the total synthesis of the actual structure of the anticancer marine natural product mycalol (2). The total synthesis of the originally proposed structure of mycalol (1) was targeted by a late-stage asymmetric dihydroxylation, which resulted in an inseparable mixture of diastereomers. Thus a new strategy was developed for the total synthesis of the revised structure of mycalol (2); all the stereocentres except the C-2′-OH were created in an asymmetric fashion by using a Maruoka allylation, a Noyori asymmetric reduction, and an asymmetric alkynylation.