Catalytic Enantioselective Approach to the Eudesmane Sesquiterpenoids: Total Synthesis of (+)-Carissone Samantha R. Levine Michael R. Krout Brian M. Stoltz 10.1021/ol802409h.s001 https://acs.figshare.com/articles/journal_contribution/Catalytic_Enantioselective_Approach_to_the_Eudesmane_Sesquiterpenoids_Total_Synthesis_of_Carissone/2885431 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. 2009-01-15 00:00:00 eudesmane sesquiterpenoids agent strategy synthesis Eudesmane Sesquiterpenoids syn stereochemistry transformation alkylation vinylogous ester substrates Catalytic Enantioselective Approach eudesmol enantioselective approach Carissone center Total Synthesis preparation calcium quaternary diastereoselective olefin hydrogenation carissone blocker