A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products

M. Todd Hovey, Daniel T. Cohen, Daniel M. Walden, Paul H.Y. Cheong, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)9864-9867
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number33
DOIs
StatePublished - 2017

Keywords

  • N-heterocyclic carbenes
  • armillaridin
  • marasmane
  • protoilludane
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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