Levine, Samantha R. and Krout, Michael R. and Stoltz, Brian M. (2009) Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone. Organic Letters, 11 (2). pp. 289-292. ISSN 1523-7060 http://resolver.caltech.edu/CaltechAUTHORS:LEVol09
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Abstract
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.
| Item Type: | Article | ||||||
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| 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 NIHNIGMS (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. | ||||||
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| Subject Keywords: | carbon quaternary stereocenters; diels-alder reactions; alpha-eudesmol; asymmetric catalysis; channel blocker; enol ethers; alkylation; carissone; aldehydes; acids | ||||||
| Record Number: | CaltechAUTHORS:LEVol09 | ||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:LEVol09 | ||||||
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| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||
| ID Code: | 13592 | ||||||
| Collection: | CaltechAUTHORS | ||||||
| Deposited By: | Tony Diaz | ||||||
| Deposited On: | 12 May 2009 20:48 | ||||||
| Last Modified: | 26 Dec 2012 10:52 |
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