Synthesis enables a structural revision of the Mycobacterium tuberculosis-produced diterpene, edaxadiene

Jillian E. Spangler, Cheryl A. Carson, Erik J. Sorensen

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

A stereodivergent synthesis of the [3.3.1] bicyclic core of edaxadiene was completed utilizing a key intramolecular oxidative ketone allylation. Significant discrepancies between the spectroscopic data obtained for the synthetic construct and the natural isolate raised questions about the structural assignment of edaxadiene. A subsequent structural reassignment was validated by completion of a total synthesis of the correct structure of the natural product.

Original languageEnglish (US)
Pages (from-to)202-205
Number of pages4
JournalChemical Science
Volume1
Issue number2
DOIs
StatePublished - Aug 2010

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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