2. Academic Validation
  3. Synthesis of the antifungal beta-1,3-glucan synthase inhibitor CANCIDAS (caspofungin acetate) from pneumocandin B0

Synthesis of the antifungal beta-1,3-glucan synthase inhibitor CANCIDAS (caspofungin acetate) from pneumocandin B0

  • J Org Chem. 2007 Mar 30;72(7):2335-43. doi: 10.1021/jo062008i.
William R Leonard Jr 1,  Kevin M Belyk,  David A Conlon,  Dean R Bender,  Lisa M DiMichele,  Ji Liu,  David L Hughes
Affiliations

Affiliation

  • 1 Process Research Department, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. [email protected]
PMID: 17343416 DOI: 10.1021/jo062008i
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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