Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions
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.
Additional Information© 2015 the Partner Organisations. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Received 26 Nov 2014, Accepted 20 Jan 2015, First published online 20 Jan 2015. The NKU authors thank the National Natural Science Foundation of China, Tianjin Natural Science Foundation (grant no. 12JCZDJC26400), the '111' project (B06005) of the Ministry of Education of China, and Program for New Century Excellent Talents in University for financial support. The Caltech authors wish to thank NIH-NIGMS (R01GM080269) for financial support. BPP is grateful to the National Science Foundation for a Graduate Research Fellowship. Toray is thanked for providing YN a postdoctoral opportunity at Caltech.
Published - c4qo00312h.pdf
Supplemental Material - c4qo00312h1_si.pdf