Synthesis of the Antifungal β-1,3-Glucan Synthase Inhibitor CANCIDAS (Caspofungin Acetate) from Pneumocandin B0
The Journal of Organic Chemistry2007Vol. 72(7), pp. 2335–2343
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William R. Leonard, Kevin M. Belyk, David A. Conlon, Dean R. Bender, Lisa DiMichele, Ji Liu, David L. Hughes
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 2 in a 45% overall yield.
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