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The Catalytic Asymmetric Total Synthesis of Elatol

White, David E. and Stewart, Ian C. and Grubbs, Robert H. and Stoltz, Brian M. (2008) The Catalytic Asymmetric Total Synthesis of Elatol. Journal of the American Chemical Society, 130 (3). pp. 810-811. ISSN 0002-7863. PMCID PMC2533138. doi:10.1021/ja710294k.

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Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.

Item Type:Article
Related URLs:
URLURL TypeDescription Information CentralArticle
Grubbs, Robert H.0000-0002-0057-7817
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2008 American Chemical Society. Received 13 November 2007. Published online 29 December 2007. Published in print 1 January 2008. We thank the NIH-NIGMS (R01 GM080269-01, R01 GM31332-05, postdoctoral fellowships to D.E.W. and I.C.S.), Abbott, Amgen, Bristol-Myers Squibb, Merck, and Caltech for generous funding; Materia, Inc. for their kind donation of catalyst 22 used in these studies; Professors Mercedes Cueto and Karen L. Erickson for their kind donation of natural samples of elatol (1); Brinton Seashore-Ludlow for experimental assistance; and Professor Peter B. Dervan and David M. Chenoweth for use of their HPLC.
Funding AgencyGrant Number
Bristol-Myers SquibbUNSPECIFIED
Issue or Number:3
PubMed Central ID:PMC2533138
Record Number:CaltechAUTHORS:20170222-082042531
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74453
Deposited By: Ruth Sustaita
Deposited On:22 Feb 2017 16:36
Last Modified:11 Nov 2021 05:27

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