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

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

doi:10.1039/c0sc00284d

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

21 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 language	English (US)
Pages (from-to)	202-205
Number of pages	4
Journal	Chemical Science
Volume	1
Issue number	2
DOIs	https://doi.org/10.1039/c0sc00284d
State	Published - Aug 2010

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1039/c0sc00284d

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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.",

author = "Spangler, \{Jillian E.\} and Carson, \{Cheryl A.\} and Sorensen, \{Erik J.\}",

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AU - Carson, Cheryl A.

AU - Sorensen, Erik J.

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N2 - 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.

AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

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