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A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products.

ABSTRACT: The Armillaria and Lactarius genera of fungi produce the antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. We report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The key features of these syntheses are 1)?the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, 2)?the utility of a key 1,2-cyclobutanediol intermediate to serve as a precursor to each natural product class, and 3)?a direct chemical conversion of a protoilludane to a marasmane through serendipitous ring contraction, which provides experimental support for their proposed biosynthetic relationships.

SUBMITTER: Hovey MT

PROVIDER: S-EPMC5682929 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products.

Hovey M Todd MT Cohen Daniel T DT Walden Daniel M DM Cheong Paul H-Y PH Scheidt Karl A KA

Angewandte Chemie (International ed. in English) 20170717 33

The Armillaria and Lactarius genera of fungi produce the antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. We report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The key features of these syntheses are 1) the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, 2) the utility of a key 1,2-cyclobutanediol intermediate to serve as a precurso ...[more]

PMID: 28632913

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