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Org Lett. 2014 Mar 21;16(6):1653-5. doi: 10.1021/ol500308e. Epub 2014 Feb 20.

Total synthesis of mersicarpine through a cationic cyclization approach.

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1
State Key Laboratory and Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin, China , 300071.

Abstract

A concise total synthesis of mersicarpine is achieved by exploiting a cyclic carbamate for generation of a tertiary carbocation. The key step involves intramolecular Friedel-Crafts alkylation with this carbocation for the construction of a quaternary carbon center and a subsequent oxidation and cyclization cascade for the formation of a seven-membered cyclic imine. The chemistry allowed for a rapid one-pot synthesis of mersicarpine from a simple intermediate using straightforward chemical operations.

PMID:
24555758
DOI:
10.1021/ol500308e
[Indexed for MEDLINE]
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