title: Total synthesis of (-)-lepistine.
abstract: The first total synthesis of (-)-lepistine has been accomplished in 11 steps from (S)-glycidol. The synthesis features construction of the 10-membered ring via an intramolecular epoxide opening by nosylamide, regioselective dehydration to form an enol ether, and construction of the aminal moiety induced by cleavage of the nosyl groups.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho , Chikusa-ku, Nagoya 464-8601, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kitabayashi
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yokoshima
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D011083:Polycyclic Compounds; D020005:Propanols; C000591955:lepistine; C004312:glycidol