Issue 7, 2012
From the journal:

Organic & Biomolecular Chemistry

Oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine†

Xiao-Yu Liu,a   Hang Cheng,a   Xiao-Huan Li,a   Qiao-Hong Chen,*a   Liang Xua  and  Feng-Peng Wang*a  

* Corresponding authors

a Department of Chemistry of Medicinal Natural Products, Sichuan University, No. 17, Duan 3, Renmin Nan Road, Chengdu
E-mail: qiaohongchen@yahoo.com.cn, wfp@scu.edu.cn
Fax: +86-28-85501368

Abstract

A convergent and efficient formal synthesis of (±)-atisine has been accomplished. The synthetic strategy is to efficiently construct the bicyclo[2.2.2]octane ring moiety by an oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade. The first total synthesis of another atisine-type C20-diterpenoid alkaloid, (±)-isoazitine, has also been achieved employing the same strategy.

Graphical abstract: Oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB06704D
Article type
Paper
Submitted
09 Oct 2011
Accepted
08 Nov 2011
First published
17 Nov 2011

Org. Biomol. Chem., 2012,10, 1411-1417

Permissions

Request permissions

Oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine

X. Liu, H. Cheng, X. Li, Q. Chen, L. Xu and F. Wang, Org. Biomol. Chem., 2012, 10, 1411 DOI: 10.1039/C1OB06704D

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements