Diastereoselective Total Synthesis of (-)-Galiellalactone
Taewoo Kim1, Young Taek Han2, Hongchan An1
1College of Pharmacy, Seoul National University , 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea.
Abstract:
An enantioselective total synthesis of (-)-galiellalactone has been accomplished. The key features of the synthesis involve the highly stereoselective construction of the cis-trisubstituted cyclopentane intermediate by a Pd(0)-catalyzed cyclization, the stereospecific introduction of an angular hydroxyl group by Riley oxidation, and the efficient construction of the tricyclic system of (-)-galiellalactone via a combination of diastereoselective Hosomi-Sakurai crotylation and ring-closing metathesis (RCM).
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