title: Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2)-mediated ring opening and bridge-forming Mannich reaction.
abstract: The first total synthesis of (+/-)-subincanadine F, a bioactive indole alkaloid structurally featuring a 1-azabicyclo[4.3.1]decane unit, has been realized from 1-(para-methoxybenzyl)tryptamine in six steps. The bridge-containing tetracyclic framework of subincanadine F was efficiently assembled by a SmI2-mediated ring opening followed by an acid-mediated Mannich reaction. In addition, the tetracyclic ketoester 6, a key intermediate potentially useful for synthesizing structurally related indole alkaloids as well, was obtained in one step from alpha,beta-diketoester 5.
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China 200032.
authors.forename: Peng
authors.initials: P
authors.lastname: Gao
authors.forename: Yanqin
authors.initials: Y
authors.lastname: Liu
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.forename: Peng-Fei
authors.initials: PF
authors.lastname: Xu
authors.forename: Shaowu
authors.initials: S
authors.lastname: Wang
authors.forename: Yong
authors.initials: Y
authors.lastname: Lu
authors.forename: Mingyuan
authors.initials: M
authors.lastname: He
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhai
mesh_terms: D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D026121:Indole Alkaloids; C522871:subincanadine F