title: Enantioselective total synthesis of (-)-walsucochin B.
abstract: The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000, P. R. China.
authors.forename: Shiyan
authors.initials: S
authors.lastname: Xu
authors.forename: Jixiang
authors.initials: J
authors.lastname: Gu
authors.forename: Huilin
authors.initials: H
authors.lastname: Li
authors.forename: Donghui
authors.initials: D
authors.lastname: Ma
authors.forename: Xingang
authors.initials: X
authors.lastname: Xie
authors.forename: Xuegong
authors.initials: X
authors.lastname: She
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D005609:Free Radicals; D015394:Molecular Structure; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D004852:Epoxy Compounds; D005609:Free Radicals; D014315:Triterpenes; C527908:walsucochin B