Issue 55, 2016
From the journal:

Chemical Communications

Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel–Crafts type cyclization†

Dong Chen,ab   Wen-Dan Xu,ab   Hao-Miao Liu,ab   Ming-Ming Li,c   Yong-Min Yan,a   Xiao-Nian Li,a   Yan Li,a   Yong-Xian Chenga  and  Hong-Bo Qin*a  

* Corresponding authors

a State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China
E-mail: qinhongbo@mail.kib.ac.cn
Fax: +86-871-65238010
Tel: +86-871-65238010

b University of Chinese Academy of Sciences, Beijing 100049, P. R. China

c Yunnan Baiyao Group Corporation Limited, Kunming 650032, China

Abstract

Enantioselective total synthesis of (+)-Lingzhiol has been achieved. It is the first example of in tandem semipinacol rearrangement reactions, the migrated aryl group further reacting with the carbonyl oxonium electrophile to furnish a polycyclic skeleton. Our synthesis involves 13 steps and proceeds in 6% overall yield.

Graphical abstract: Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel–Crafts type cyclization

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C6CC03764J
Article type
Communication
Submitted
05 May 2016
Accepted
06 Jun 2016
First published
06 Jun 2016

Chem. Commun., 2016,52, 8561-8564

Permissions

Request permissions

Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel–Crafts type cyclization

D. Chen, W. Xu, H. Liu, M. Li, Y. Yan, X. Li, Y. Li, Y. Cheng and H. Qin, Chem. Commun., 2016, 52, 8561 DOI: 10.1039/C6CC03764J

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