Issue 97, 2015
From the journal:

Chemical Communications

Domino intramolecular Diels–Alder reactions to construct a 6/6/5/5 fused tetracyclic framework†

Gaoyuan Zhao,a   Min He,a   Huilin Li,a   Shuangshuang Duan,a   Ziyun Yuan,a   Xingang Xiea  and  Xuegong She*abc  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, China
E-mail: shexg@lzu.edu.cn

b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, China

c State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China

Abstract

Domino intramolecular Diels–Alder (IMDA) reactions towards the 6/6/5/5 fused tetracyclic natural products were developed in satisfactory yield and high stereoselectivity. Four rings, six contiguous stereocenters and four C–C bonds were formed in a single operation. 4-epi-Hydromitchellene B was also synthesised efficiently via this strategy.

Graphical abstract: Domino intramolecular Diels–Alder reactions to construct a 6/6/5/5 fused tetracyclic framework

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Article information

DOI
https://doi.org/10.1039/C5CC06923H
Article type
Communication
Submitted
18 Aug 2015
Accepted
05 Oct 2015
First published
06 Oct 2015

Chem. Commun., 2015,51, 17321-17323

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Domino intramolecular Diels–Alder reactions to construct a 6/6/5/5 fused tetracyclic framework

G. Zhao, M. He, H. Li, S. Duan, Z. Yuan, X. Xie and X. She, Chem. Commun., 2015, 51, 17321 DOI: 10.1039/C5CC06923H

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