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.
MeSH terms
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Amides / chemistry
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Amines / chemistry
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Antifungal Agents / chemical synthesis*
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Antifungal Agents / chemistry
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Antifungal Agents / isolation & purification
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Caspofungin
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Chromatography, High Pressure Liquid
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Echinocandins
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Glucosyltransferases / antagonists & inhibitors*
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Lipopeptides
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Molecular Structure
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Peptides, Cyclic / chemical synthesis*
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Peptides, Cyclic / chemistry*
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Peptides, Cyclic / isolation & purification
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Sulfhydryl Compounds / chemistry
Substances
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Amides
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Amines
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Antifungal Agents
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Echinocandins
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Lipopeptides
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Peptides, Cyclic
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Sulfhydryl Compounds
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pneumocandin B(0)
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Glucosyltransferases
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1,3-beta-glucan synthase
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Caspofungin