Total synthesis of C19-diterpenoid alkaloid: construction of a functionalized ABCDE-ring system

Mengchen Liu; Chuanxu Cheng; Weiyan Xiong; Hang Cheng; Jian-Li Wang; Liang Xu

doi:10.1039/C8QO00143J

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Total synthesis of C₁₉-diterpenoid alkaloid: construction of a functionalized ABCDE-ring system†

Mengchen Liu,‡^a Chuanxu Cheng,‡^a Weiyan Xiong,^a Hang Cheng,^a Jian-Li Wang*^b and Liang Xu

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Drug Targeting, Ministry of Education, and Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu 610041, P. R. China
E-mail: liangxu@scu.edu.cn

^b State Key Laboratory of Oral Disease, West China School of Stomatology, Sichuan University, Chengdu 610041, P. R. China
E-mail: wangjianli0804@163.com

Abstract

A synthetic approach for the ABCDE ring system of methyllycaconitine starting from a BCD tricycle precursor 14 was described. The synthesis features a useful strategy for the full functionalization of ring B, a 1,7-enyne reductive radical cyclization for the construction of ring A, and a straightforward double condensation for installation of the piperidine ring E.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C8QO00143J
Article type: Research Article
Submitted: 06 Feb 2018
Accepted: 14 Mar 2018
First published: 15 Mar 2018

Download Citation

Org. Chem. Front., 2018,5, 1502-1505

Permissions

Request permissions

Total synthesis of C₁₉-diterpenoid alkaloid: construction of a functionalized ABCDE-ring system

M. Liu, C. Cheng, W. Xiong, H. Cheng, J. Wang and L. Xu, Org. Chem. Front., 2018, 5, 1502 DOI: 10.1039/C8QO00143J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic Chemistry Frontiers