Issue 18, 2015
From the journal:

Organic & Biomolecular Chemistry

Concise total synthesis of (±)-aspidospermidine†

Haichen Ma,a   Xingang Xie,a   Peng Jing,a   Weiwei Zhanga  and  Xuegong She*ab  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China
E-mail: shexg@lzu.edu.cn

b Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P.R. China

Abstract

(±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the synthesis of other Aspidosperma alkaloids.

Graphical abstract: Concise total synthesis of (±)-aspidospermidine

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Article information

DOI
https://doi.org/10.1039/C5OB00228A
Article type
Paper
Submitted
03 Feb 2015
Accepted
19 Mar 2015
First published
24 Mar 2015

Org. Biomol. Chem., 2015,13, 5255-5259

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Concise total synthesis of (±)-aspidospermidine

H. Ma, X. Xie, P. Jing, W. Zhang and X. She, Org. Biomol. Chem., 2015, 13, 5255 DOI: 10.1039/C5OB00228A

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