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  • Title: Total synthesis of cis-solamin: exploiting the RuO4-catalyzed oxidative cyclization of dienes.
    Author: Göksel H, Stark CB.
    Journal: Org Lett; 2006 Aug 03; 8(16):3433-6. PubMed ID: 16869628.
    Abstract:
    [structure: see text] An enantioselective total synthesis of cis-solamin has been accomplished using a highly diastereoselective ruthenium tetroxide catalyzed oxidative cyclization as a crucial transformation. Further key steps involved an enzymatic desymmetrization, a TPAP-catalyzed oxidative termini differentiation, and a ruthenium-catalyzed Alder-ene reaction. Thus, the total synthesis of cis-solamin was achieved in 11 steps with an overall yield of 7.5%.
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