title: Total synthesis of cis-solamin.
abstract: [structure: see text] A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)2-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.
authors.affiliation: Graduate School of Agriculture, Sciences of Functional Foods, Integrated Department, Shinshu University, 8304 Mimamiminowa Kamiina, Nagano 399-4598, Japan. makabeh@gipmc.shinshu-u.ac.jp
authors.forename: Hidefumi
authors.initials: H
authors.lastname: Makabe
authors.forename: Yasunao
authors.initials: Y
authors.lastname: Hattori
authors.forename: Akira
authors.initials: A
authors.lastname: Tanaka
authors.forename: Takayuki
authors.initials: T
authors.lastname: Oritani
mesh_terms: D029061:Annonaceae / Q000737:chemistry*; D001558:Benzethonium / Q000138:chemical synthesis*; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D007202:Indicators and Reagents; D001558:Benzethonium