期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 33, 页码 9864-9867出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705308
关键词
armillaridin; marasmane; N-heterocyclic carbenes; protoilludane; total synthesis
资金
- NIGMS [R01-GM073072]
- ACS Division of Organic Chemistry Fellowship
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.
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