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PMID: 19093809 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

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

Organic letters ·Vol. 11 ·No. 2 ·2009-01-15 ·Pages 289-92

Levine SR, Krout MR, Stoltz BM

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 (-)-alpha-eudesmol.

MeSH Terms
Anti-Bacterial Agents/chemical synthesis,chemistry Calcium Channel Blockers/chemical synthesis,chemistry Catalysis Palladium/chemistry Sesquiterpenes, Eudesmane/chemical synthesis,chemistry Stereoisomerism Substrate Specificity
Chemicals
Anti-Bacterial Agents Calcium Channel Blockers Sesquiterpenes, Eudesmane carissone Palladium
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Levine Samantha R
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Krout Michael R
Stoltz Brian M
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Article Info
Journal
Organic letters
Abbr.
Org Lett
ISSN
1523-7052
DOI
10.1021/ol802409h
Published
2009-01-15
Pages
289-92
Language
English
Region
United States
NLM ID
100890393
PMCID
PMC2724392
Subset
IM
Grants
NIGMS NIH HHS · R01 GM080269 · United States
NIGMS NIH HHS · R01 GM080269-02 · United States
NIGMS NIH HHS · R01GM080269-01 · United States
External Links
PubMed source DOI: 10.1021/ol802409h PMC Full Text View journal details
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