Organic letters

Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone

SR Levine, MR Krout, BM Stoltz

Index: Levine, Samantha R.; Krout, Michael R.; Stoltz, Brian M. Organic Letters, 2009 , vol. 11, # 2 p. 289 - 292

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Citation Number: 57

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 (+)- ...