Total synthesis of (+)-crocacin D

Abstract

The first total synthesis of the potent antifungal and cytotoxic agent (+)-crocacin D in optically pure form following a convergent strategy is described here. The regioselective ring opening of a silyl-substituted epoxide with an azide ion, based on a method developed by us earlier, and subsequent subjection of the resulting α-azido-β-hydroxyalkylsilane intermediate to a Peterson elimination reaction at an appropriate stage during the synthesis constituted the key steps for the stereoselective construction of the crucial cis enamide moiety of the molecule.