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

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.

SUBMITTER: Spangler JE 

PROVIDER: S-EPMC3221386 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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

Spangler Jillian E JE   Carson Cheryl A CA   Sorensen Erik J EJ  

Chemical science 20100601 2

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. ...[more]

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