title: SmI2-mediated radical coupling strategy to Securinega alkaloids: total synthesis of (-)-14,15-dihydrosecurinine and formal total synthesis of (-)-securinine.
abstract: The asymmetric total synthesis of (-)-14,15-dihydrosecurinine and the formal total synthesis of (-)-securinine were accomplished starting from an easily available malimide. A concise SmI2-mediated radical coupling strategy has been developed to construct the bridged α-hydroxy 6-azabicyclo[3.2.1]octanone in four steps with high diastereoselectivity.
authors.affiliation: Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen, Fujian 361005, China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Zheng
authors.forename: Juan
authors.initials: J
authors.lastname: Liu
authors.forename: Chen-Xi
authors.initials: CX
authors.lastname: Ye
authors.forename: Ao
authors.initials: A
authors.lastname: Wang
authors.forename: Ai-E
authors.initials: AE
authors.lastname: Wang
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D019665:Euphorbiaceae / Q000737:chemistry*; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D053961:Azabicyclo Compounds; D001381:Azepines; D006572:Heterocyclic Compounds, Bridged-Ring; D007202:Indicators and Reagents; D007783:Lactones; D010880:Piperidines; C000600032:alpha-hydroxy 6-azabicyclo(3.2.1)octanone; C000785:securinine