title: Synthetic studies of the lichen macrolide lepranthin. Stereoselective synthesis of the diolide framework based on regioselective epoxide-opening reactions.
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.
authors.affiliation: Department of Applied Chemistry, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo, Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Takada
authors.forename: Shinji
authors.initials: S
authors.lastname: Nagumo
authors.forename: Eiko
authors.initials: E
authors.lastname: Yasui
authors.forename: Megumi
authors.initials: M
authors.lastname: Mizukami
authors.forename: Masaaki
authors.initials: M
authors.lastname: Miyashita
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D008011:Lichens / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D004852:Epoxy Compounds; D018942:Macrolides; D012717:Sesquiterpenes