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Published January 15, 2009 | Accepted Version + Supplemental Material
Journal Article Open

Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone


A catalytic enantioselective approach to the eudesmane sesquiterpenoids is reported. The strategic use of a palladium-catalyzed enantioselective alkylation of vinylogous ester substrates forged the C(10) all-carbon quaternary center. This key transformation enabled a diastereoselective olefin hydrogenation to create the syn stereochemistry at C(7). The devised synthetic strategy allowed for the preparation of the antibacterial agent (+)-carissone and a formal synthesis of the P/Q-type calcium channel blocker (-)-α-eudesmol.

Additional Information

© 2008 American Chemical Society. Received October 19, 2008. We thank Krastina V. Petrova and Justin T. Mohr (Caltech) for helpful discussions and experimental assistance. We gratefully acknowledge the NIH-NIGMS (RO1GM080269-01), Marcella R. Bonsall and the Dalton Fund (undergraduate fellowships to S.R.L.), Eli Lilly (predoctoral fellowship to M.R.K.), Amgen, Abbott Laboratories, Boehringer-Ingelheim, Materia, Merck, Bristol-Meyers Squibb, and the California Institute of Technology for financial support.

Attached Files

Accepted Version - nihms110342.pdf

Supplemental Material - LEVol09supp.pdf


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