Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone.
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.
Levine
Samantha R
SR
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
MR
Stoltz
Brian M
BM
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
D000900:Anti-Bacterial Agents; D002121:Calcium Channel Blockers; D045787:Sesquiterpenes, Eudesmane; C538844:carissone; D010165:Palladium