AI Article Synopsis
- - A new three-step method for synthesizing the antifungal drug CANCIDAS (caspofungin acetate) starting from pneumocandin B0 is detailed in the study.
- - Key features of the synthesis involve creating a specific compound called phenylthioaminal, effectively reducing a primary amide in a single step with borane, and selectively substituting it with ethylenediamine.
- - The overall yield of the final product, CANCIDAS, achieved through this synthesis is 45%, highlighting its efficiency.
Article 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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| http://dx.doi.org/10.1021/jo062008i | DOI Listing |
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