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

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. PMCID PMC2724392. 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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol802409hDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol802409hPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2724392/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHRO1GM080269-01
Dalton FundUNSPECIFIED
Eli LillyUNSPECIFIED
AmgenUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Materia, Inc.UNSPECIFIED
MerckUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:carbon quaternary stereocenters; diels-alder reactions; alpha-eudesmol; asymmetric catalysis; channel blocker; enol ethers; alkylation; carissone; aldehydes; acids
PubMed Central ID:PMC2724392
Record Number:CaltechAUTHORS:LEVol09
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:LEVol09
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:15 Feb 2017 19:49

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