title: Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B.
abstract: The C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels-Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Liang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Liyan
authors.initials: L
authors.lastname: Zhou
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Long
authors.initials: L
authors.lastname: Min
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Weijian
authors.initials: W
authors.lastname: Ye
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Wenli
authors.initials: W
authors.lastname: Bao
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Wenjing
authors.initials: W
authors.lastname: Ma
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Qianqian
authors.initials: Q
authors.lastname: Yang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Qiao
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Xinhao
authors.identifier: 0000-0002-8210-2531
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Chi-Sing
authors.identifier: 0000-0002-3564-8224
authors.initials: CS
authors.lastname: Lee
mesh_terms: D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011753:Pyrones; C543083:basiliolide B