title: Development of the intramolecular Prins cyclization/Schmidt reaction for the construction of the azaspiro[4,4]nonane: application to the formal synthesis of (±)-stemonamine.
abstract: A TiCl(4)-promoted tandem intramolecular Prins cyclization/Schmidt reaction has been designed and developed to be an efficient method for the construction of the azaspiro[4,4]nonane. The present tandem protocol has been employed to construct the tricyclic azaquaternary skeleton (ring A, B, and C) of stemonamine.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Zhi-Hua
authors.initials: ZH
authors.lastname: Chen
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D041901:Stemonaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000473:Alkanes; D001381:Azepines; D013141:Spiro Compounds; C530508:stemonamine; D015107:4-Butyrolactone; C017573:nonane