title: Divergent and efficient syntheses of the Lycopodium alkaloids (-)-lycojaponicumin C, (-)-8-deoxyserratinine, (+)-fawcettimine, and (+)-fawcettidine.
abstract: Four from one: The four title alkaloids (structures shown in blue box) have been synthesized by using a common versatile intermediate with a 6/5/5 tricyclic skeleton. This tricyclic intermediate could be easily assembled by using an intramolecular carbene addition/cyclization and a Dieckmann condensation/Tsuji-Trost allylation as key steps.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China).
authors.forename: Si-Hua
authors.initials: SH
authors.lastname: Hou
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Lin
authors.initials: L
authors.lastname: Liu
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Wang
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C524731:fawcettimine
keywords: Schmidt reaction; alkaloids; aza-Wittig reaction; divergent synthesis; natural products