Total synthesis of (+)-crocacin D

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 alpha-azido-beta-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. (C) 2002 Published by Elsevier Science Ltd.