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  • Title: Stereoselective synthesis of 7-epi-incarvilline.
    Author: Seo H, Yun H, Lee S, Jang J, Han YT, Kim DD, Lee J, Suh YG.
    Journal: Org Lett; 2013 Feb 01; 15(3):531-3. PubMed ID: 23343424.
    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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