Issue 51, 2018, Issue in Progress
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RSC Advances

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs†

Bo Zheng,a   Hui-Ya Qu,a   Tian-Zhuo Meng,a   Xia Lu,a   Jie Zheng,a   Yun-Gang He,a   Qi-Qi Fana  and  Xiao-Xin Shi ORCID logo *a  

* Corresponding authors

a Shanghai Key Laboratory of Chemical Biology and Department of Pharmaceutical Engineering, School of Pharmacy, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. China
E-mail: xxshi@ecust.edu.cn

Abstract

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.

Graphical abstract: Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

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Article information

DOI
https://doi.org/10.1039/C8RA05338C
Article type
Paper
Submitted
21 Jun 2018
Accepted
06 Aug 2018
First published
14 Aug 2018
This article is Open Access
Creative Commons BY license

RSC Adv., 2018,8, 28997-29007

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Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

B. Zheng, H. Qu, T. Meng, X. Lu, J. Zheng, Y. He, Q. Fan and X. Shi, RSC Adv., 2018, 8, 28997 DOI: 10.1039/C8RA05338C

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