Published January 15, 2009
| Version Accepted Version + Supplemental Material
Journal Article
Open
Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone
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1.
California Institute of Technology
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.
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
Files
LEVol09supp.pdf
Additional details
Identifiers
- PMCID
- PMC2724392
- Eprint ID
- 13592
- DOI
- 10.1021/ol802409h
- Resolver ID
- CaltechAUTHORS:LEVol09
Related works
- Describes
- 10.1021/ol802409h (DOI)
Funding
- NIH
- RO1GM080269-01
- Dalton Fund
- Eli Lilly
- Amgen
- Abbott Laboratories
- Boehringer-Ingelheim
- Materia, Inc.
- Merck
- Bristol-Myers Squibb
- Caltech
Dates
- Created
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2009-05-12Created from EPrint's datestamp field
- Updated
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2021-11-08Created from EPrint's last_modified field