Issue 12, 2011
From the journal:

Chemical Communications

Alkyne-mediated domino hydroformylation/double cyclization: mechanistic insight and synthesis of (±)-tashiromine†

Wen-Hua Chiou,*a   Yi-Huei Lin,a   Guei-Tang Chen,a   Yu-Kai Gao,a   Yu-Che Tseng,a   Chien-Lun Kaoa  and  Jui-Chi Tsaia  

* Corresponding authors

a Department of Chemistry, National Chung Hsing University, Taichung, Taiwan, ROC
E-mail: wchiou@dragon.nchu.edu.tw
Fax: +886-4 22862547
Tel: +886-4-22840411-420

Abstract

A novel domino reaction, alkyne-mediated domino hydroformylation/double cyclization, has been developed for rapid preparation of indolizidine type alkaloids. DFT calculations were applied for rationales of reactivity and selectivity. A concise synthesis of tashiromine as the application of the methodology is also reported.

Graphical abstract: Alkyne-mediated domino hydroformylation/double cyclization: mechanistic insight and synthesis of (±)-tashiromine

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Article information

DOI
https://doi.org/10.1039/C0CC05646D
Article type
Communication
Submitted
17 Dec 2010
Accepted
01 Feb 2011
First published
16 Feb 2011

Chem. Commun., 2011,47, 3562-3564

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Alkyne-mediated domino hydroformylation/double cyclization: mechanistic insight and synthesis of (±)-tashiromine

W. Chiou, Y. Lin, G. Chen, Y. Gao, Y. Tseng, C. Kao and J. Tsai, Chem. Commun., 2011, 47, 3562 DOI: 10.1039/C0CC05646D

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