title: Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of1H and13C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.
abstract: Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids bearing distinctive core structures were achieved through Staudinger reactions using a common intermediate. In the key cyclization step, water functioned like a switch to control which core structure to produce. The chemistry allowed for selective syntheses of the group of alkaloids from a simple intermediate through straightforward chemical operations.
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: lianggx@nankai.edu.cn.
authors.forename: Zining
authors.initials: Z
authors.lastname: Li
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: lianggx@nankai.edu.cn.
authors.forename: Qian
authors.initials: Q
authors.lastname: Geng
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: lianggx@nankai.edu.cn.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Lv
authors.affiliation: The Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu.
authors.forename: Beau P
authors.initials: BP
authors.lastname: Pritchett
authors.affiliation: The Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu.
authors.forename: Katsuaki
authors.initials: K
authors.lastname: Baba
authors.affiliation: The Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu.
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Numajiri
authors.affiliation: The Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu.
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: lianggx@nankai.edu.cn.
authors.forename: Guangxin
authors.initials: G
authors.lastname: Liang