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Stereoselective synthesis of 7-epi-incarvilline
Hyowon Seo1, Hwayoung Yun, Sujin Lee
1College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Abstract:
The enantioselective synthesis of 7-epi-incarvilline for formal syntheses of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine is described. The key features of our synthesis involve (1) stereoselective construction of the optically active bicyclic lactone utilizing Pd(0)-catalyzed allylic alkylation, (2) efficient transformation of the bridged bicyclic lactone to the key bicyclic lactam skeleton, and (3) stereoselective elaborations of two stereocenters via a substrate-controlled catalytic hydrogenation and a 1,4-addition.
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