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Issue 2, 2010
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Synthesis enables a structural revision of the Mycobacterium tuberculosis-produced diterpene, edaxadiene

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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.

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

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Publication details

The article was received on 27 Apr 2010, accepted on 29 Apr 2010 and first published on 11 Jun 2010


Article type: Edge Article
DOI: 10.1039/C0SC00284D
Citation: Chem. Sci., 2010,1, 202-205

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

    J. E. Spangler, C. A. Carson and E. J. Sorensen, Chem. Sci., 2010, 1, 202
    DOI: 10.1039/C0SC00284D

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