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Takada, H., S. Nagumo, E. Yasui, M. Mizukami & M. Miyashita 2011: Synthetic studies of the lichen Macrolide lepranthin. Stereoselective synthesis of the diolide framework based on regioselective epoxide-opening reactions. - Chemical and Pharmaceutical Bulletin 59(4): 525-527. [RLL List # 223 / Rec.# 33000]
Abstract: Stereoselective synthesis of the 16-membered diolide 27, a fully functionalized congener of lepranthin (1), is described. The requisite five asymmetric carbon centers in monomer 23 were constructed in a highly stereoselective manner by using different epoxide-opening reactions of α,β-unsaturated γ,δ-epoxy esters and epoxy alcohol derivatives as the key steps. The monomer 23 was successfully transformed into the MOM protected diolide 27 by Yamaguchi macrolactonization

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