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Synthesis and antifungal properties of papulacandin derivatives.

ABSTRACT: Derivatives of an antifungal agent that targets the ?-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid.

SUBMITTER: van der Kaaden M

PROVIDER: S-EPMC3388860 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Synthesis and antifungal properties of papulacandin derivatives.

van der Kaaden Marjolein M Breukink Eefjan E Pieters Roland J RJ

Beilstein journal of organic chemistry 20120514

Derivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the numb ...[more]

PMID: 23015820

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