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