title: Tandem semipinacol-type 1,2-carbon migration/aldol reaction toward the construction of [5-6-7] all-carbon tricyclic core of Calyciphylline A-type alkaloids.
abstract: A Lewis acid promoted tandem semipinacol-type 1,2-carbon migration/aldol reaction of trimethylsilane-protected vinylogous α-ketols with aldehyde or dimethyl acetals is reported. This reaction provides a direct and rapid way for the construction of 6-substituted spiro[4.5]decanes which extensively exist in Daphniphyllum alkaloids. By the use of this method, further construction of a [5-6-7] all-carbon tricyclic core of Calyciphylline A-type alkaloids was also completed.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Ming
authors.initials: M
authors.lastname: Yang
authors.forename: Lin
authors.initials: L
authors.lastname: Wang
authors.forename: Zheng-He
authors.initials: ZH
authors.lastname: He
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Wang
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011083:Polycyclic Compounds; C479143:calyciphylline A; D002244:Carbon