title: Total synthesis of (-)-stemonine.
abstract: [reaction: see text] An enantioselective total synthesis of (-)-stemonine (1) is reported via a convergent assembly of the acyclic precursor 2. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an iodine-induced tandem cyclization to construct the pyrrolidino-butyrolactone framework.
authors.affiliation: Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.forename: Khalida
authors.initials: K
authors.lastname: Shamim
authors.forename: Jayachandra P
authors.initials: JP
authors.lastname: Reddy
authors.forename: George S
authors.initials: GS
authors.lastname: Amato
authors.forename: Stephen M
authors.initials: SM
authors.lastname: Shaw
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000737:chemistry; D003500:Cyclization; D007455:Iodine / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D007783:Lactones; D011759:Pyrrolidines; C483261:stemonine; D007455:Iodine; C048618:hexahydroazepine