Issue 6, 2014
From the journal:

Organic Chemistry Frontiers

Asymmetric synthesis of (S)-tylophorine and (S)-cryptopleurine via one-pot Curtius rearrangement and Friedel–Crafts reaction tandem sequence†

Fazhong Chen,a   Bo Sua  and  Qingmin Wang*a  

* Corresponding authors

a State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, People's Republic of China
E-mail: wang98h@263.net, wangqm@nankai.edu.cn

Abstract

A general and practical enantioselective synthetic approach to both the phenanthroindolizidine and phenanthroquinolizidine alkaloids (S)-tylophorine and (S)-cryptopleurine was developed, which features a stereoselective alkylation and a one-pot Curtius reaction rearrangement/intramolecular cyclization cascade sequence.

Graphical abstract: Asymmetric synthesis of (S)-tylophorine and (S)-cryptopleurine via one-pot Curtius rearrangement and Friedel–Crafts reaction tandem sequence

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Article information

DOI
https://doi.org/10.1039/C4QO00084F
Article type
Research Article
Submitted
21 Mar 2014
Accepted
20 May 2014
First published
21 May 2014

Org. Chem. Front., 2014,1, 674-677

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Asymmetric synthesis of (S)-tylophorine and (S)-cryptopleurine via one-pot Curtius rearrangement and Friedel–Crafts reaction tandem sequence

F. Chen, B. Su and Q. Wang, Org. Chem. Front., 2014, 1, 674 DOI: 10.1039/C4QO00084F

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