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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Synthetic Studies of the Lichen Macrolide Lepranthin. Stereoselective Synthesis of the Diolide Framework Based on Regioselective Epoxide-Opening Reactions