title: Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone.
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.
authors.affiliation: The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: Samantha R
authors.initials: SR
authors.lastname: Levine
authors.forename: Michael R
authors.initials: MR
authors.lastname: Krout
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002121:Calcium Channel Blockers / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D010165:Palladium / Q000737:chemistry; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000900:Anti-Bacterial Agents; D002121:Calcium Channel Blockers; D045787:Sesquiterpenes, Eudesmane; C538844:carissone; D010165:Palladium