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  • Title: Enantioselective Total Synthesis of (+)-Steenkrotin A and Determination of Its Absolute Configuration.
    Author: Pan S, Gao B, Hu J, Xuan J, Xie H, Ding H.
    Journal: Chemistry; 2016 Jan 18; 22(3):959-70. PubMed ID: 26660855.
    Abstract:
    The first enantioselective total synthesis of (+)-steenkrotin A has been achieved in 18 steps and 4.2 % overall yield. The key features of the strategy entail a Rh-catalyzed O-H bond insertion followed by an intramolecular carbonyl-ene reaction, two sequential SmI2 -mediated Ueno-Stork and ketyl-olefin cyclizations, and a cascade intramolecular aldol condensation/vinylogous retro-aldol/aldol process with inversion of the relative configuration at the C7 position. The absolute configuration of (+)-steenkrotin A was determined based on the stepwise construction of the stereocenters during the total synthesis.
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