Issue 2, 2010
From the journal:

Chemical Science

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

Jillian E. Spangler,a   Cheryl A. Carsona  and  Erik J. Sorensen*a  

* Corresponding authors

a Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, NJ, USA
E-mail: ejs@princeton.edu

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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Article information

DOI
https://doi.org/10.1039/C0SC00284D
Article type
Edge Article
Submitted
27 Apr 2010
Accepted
29 Apr 2010
First published
11 Jun 2010

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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