Synthesis of the Antifungal β-1, 3-Glucan Synthase Inhibitor CANCIDAS (Caspofungin Acetate) from Pneumocandin B0

…, DA Conlon, DR Bender, LM DiMichele…

Index: Leonard Jr., William R.; Belyk, Kevin M.; Conlon, David A.; Bender, Dean R.; DiMichele, Lisa M.; Liu, Ji; Hughes, David L. Journal of Organic Chemistry, 2007 , vol. 72, # 7 p. 2335 - 2343

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Citation Number: 33

Abstract

A novel three-step synthesis of the highly functionalized antifungal agent CANCIDAS (caspofungin acetate, 2) is described, starting from the natural product pneumocandin B0 (1). The highlights of the synthesis include a stereoselective formation of a phenylthioaminal, a remarkable chemoselective, high-yielding, one-step borane reduction of a primary amide, and a stereoselective substitution of the phenylthioaminal with ethylenediamine producing ...