title: Highly efficient and stereoselective N-vinylation of oxiranecarboxamides and unprecedented 8-endo-epoxy-arene cyclization: expedient and biomimetic synthesis of some Clausena alkaloids.
abstract: [structure: see text]. Catalyzed by CuI/N,N-dimethylglycine, oxiranecarboxamides underwent a highly efficient and stereoselective N-vinylation reaction with (Z)-1-aryl-2-bromoethenes to afford the corresponding enamides. The method has been applied to a straightforward synthesis of (-)-(2R,3S)-SB204900, the enantiomer of the natural product. Following a hypothetic biomimetic pathway, both (+)-(5R,6S)-xi-Clausenamide and (-)-(5R,6S)-balasubramide have been efficiently synthesized for the first time through the unprecedented intramolecular 8-endo-epoxy-arene cyclization of (Z)-N-(phenylvinyl)oxiranecarboxamides.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China.
authors.forename: Luo
authors.initials: L
authors.lastname: Yang
authors.forename: Gang
authors.initials: G
authors.lastname: Deng
authors.forename: De-Xian
authors.initials: DX
authors.lastname: Wang
authors.forename: Zhi-Tang
authors.initials: ZT
authors.lastname: Huang
authors.forename: Jie-Ping
authors.initials: JP
authors.lastname: Zhu
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000302:isolation & purification; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D027821:Rutaceae / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000577:Amides; D004852:Epoxy Compounds; D008024:Ligands; D014753:Vinyl Compounds; C003763:vinyl bromide