title: General and efficient strategy for erythrinan and homoerythrinan alkaloids: syntheses of (+/-)-3-demethoxyerythratidinone and (+/-)-erysotramidine.
abstract: [reaction: see text] A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides followed by a N-acyliminium ion promoted intramolecular cyclization, and represents one of the shortest routes to erythrinan and homoerythrinan alkaloids. As the application, the formal total synthesis of (+/-)-3-demethoxyerythratidinone and the total synthesis of (+/-)-erysotramidine have been achieved, respectively.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, PRC.
authors.forename: Shuanhu
authors.initials: S
authors.lastname: Gao
authors.forename: Yong Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Xiangdong
authors.initials: X
authors.lastname: Hu
authors.forename: Shaohua
authors.initials: S
authors.lastname: Wang
authors.forename: Rongbao
authors.initials: R
authors.lastname: Hua
authors.forename: Yijun
authors.initials: Y
authors.lastname: Jiang
authors.forename: Yuming
authors.initials: Y
authors.lastname: Zhao
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Fan
authors.forename: Shuyu
authors.initials: S
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004895:Erythrina / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C514302:3-demethoxyerythratidinone; D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D026121:Indole Alkaloids; C492626:erysotramidine