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Published January 23, 2008 | Supplemental Material + Accepted Version
Journal Article Open

The Catalytic Asymmetric Total Synthesis of Elatol


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.

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.

Attached Files

Accepted Version - nihms62867.pdf

Supplemental Material - ja710294k-file002.pdf


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