Published in
Org. Chem. Front., 3(2), p. 236-240
DOI: 10.1039/c4qo00312h
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Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions
Journal article published in 2015 by
Zining Li 
,
Qian Geng,
Zhe Lv,
Beau P. Pritchett,
Katsuaki Baba,
Yoshitaka Numajiri,
Brian M. Stoltz,
Guangxin Liang
,
Qian Geng,
Zhe Lv,
Beau P. Pritchett,
Katsuaki Baba,
Yoshitaka Numajiri,
Brian M. Stoltz,
Guangxin Liang
This paper is made freely available by the publisher.
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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.