title: Total syntheses of (-)-huperzine Q and (+)-lycopladines B and C.
abstract: Utilizing a late-stage enamine bromofunctionalization strategy, the twelve-step total synthesis of (-)-huperzine Q was accomplished. Furthermore, the first total syntheses of (+)-lycopladines B and C are described. An unprecedented X-ray crystal structure of an unusual epoxyamine intermediate is also reported, and the synthetic application of this intermediate in natural product synthesis is demonstrated.
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072 (China); National Institute of Biological Sciences (NIBS), Beijing 102206 (China).
authors.forename: Benke
authors.initials: B
authors.lastname: Hong
authors.forename: Houhua
authors.initials: H
authors.lastname: Li
authors.forename: Jinbao
authors.initials: J
authors.lastname: Wu
authors.forename: Jing
authors.initials: J
authors.lastname: Zhang
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Lei
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; D003509:Cyclohexanecarboxylic Acids; D006576:Heterocyclic Compounds, 4 or More Rings; D007659:Ketones; D013141:Spiro Compounds; C578574:huperzine-Q; C044895:cyclohexanecarboxylic acid
keywords: alkaloids; epoxyamines; metathesis; natural products; total synthesis