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 of (1)H and (13)C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

Zining Li,Geng Q,Zhe Lv,Beau P. Pritchett,Baba K,Yoshitaka Numajiri,Brian M. Stoltz,Guangxin Liang

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 of (1)H and (13)C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

2015

Zining Li
Geng Q
Zhe Lv
Beau P. Pritchett
Baba K
Yoshitaka Numajiri
Brian M. Stoltz
Guangxin Liang

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.

Keywords:

Mersicarpine
Combinatorial chemistry
Nanotechnology
Carbon-13 NMR
Leuconolam
Leuconoxine
Engineering

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