Catalytic Enantioselective Approach to the Eudesmane Sesquiterpenoids: Total Synthesis of (+)-Carissone
- 18 December 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (2) , 289-292
- https://doi.org/10.1021/ol802409h
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 (−)-α-eudesmol.Keywords
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