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

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...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2010-06, Vol.1 (2), p.202-205
Main Authors: Spangler, Jillian E, Carson, Cheryl A, Sorensen, Erik J
Format: Article
Language:English
Subjects:
Data processing
Mycobacterium
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c0sc00284d