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  • Title: Total synthesis and stereochemical reassignment of mandelalide A.
    Author: Lei H, Yan J, Yu J, Liu Y, Wang Z, Xu Z, Ye T.
    Journal: Angew Chem Int Ed Engl; 2014 Jun 16; 53(25):6533-7. PubMed ID: 24838194.
    Abstract:
    The total synthesis of the tunicate metabolite mandelalide A and the correction of its originally assigned stereochemistry are reported. Key features of the convergent, fully stereocontrolled route include the use of a Prins cyclization for the diastereoselective construction of the tetrahydropyran subunit, Rychnovsky-Bartlett cyclization for the preparation of the tetrahydrofuran moiety, Suzuki coupling, Horner-Wadsworth-Emmons macrocyclization, and glycosylation to append the L-rhamnose-derived pyranoside.
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