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

Samantha R Levine; Michael R Krout; Brian M Stoltz

doi:10.1021/ol802409h

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

Org Lett. 2009 Jan 15;11(2):289-92. doi: 10.1021/ol802409h.

Authors

Samantha R Levine¹, Michael R Krout, Brian M Stoltz

Affiliation

¹ The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Calcium Channel Blockers / chemical synthesis
Calcium Channel Blockers / chemistry
Catalysis
Palladium / chemistry
Sesquiterpenes, Eudesmane / chemical synthesis*
Sesquiterpenes, Eudesmane / chemistry
Stereoisomerism
Substrate Specificity

Substances

Anti-Bacterial Agents
Calcium Channel Blockers
Sesquiterpenes, Eudesmane
carissone
Palladium

Abstract

Publication types

MeSH terms

Substances

Grants and funding