Issue 44, 2017
From the journal:

Chemical Communications

A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes†

Liyan Song, ORCID logo *a   Fang Huang,a   Liwen Guo,a   Ming-An Ouyanga  and  Rongbiao Tong ORCID logo *b  

* Corresponding authors

a State Key Laboratory of Ecological Pest Control for Fujian and Taiwan Crops, Institute of Plant Virology, Fujian Agriculture and Forestry University, Fuzhou, Fujian, China
E-mail: songliyan@fafu.edu.cn

b Department of Chemistry, The Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China
E-mail: rtong@ust.hk

Abstract

A new approach has been developed for the synthesis of 8-substituted 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/o-quinone methide formation/6π-electrocyclization. This new method was demonstrated with 28 examples tolerating different substitutions at alkenes, allylic and aromatic ring and with total syntheses of three 2H-chromene natural products.

Graphical abstract: A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes

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Article information

DOI
https://doi.org/10.1039/C7CC03037A
Article type
Communication
Submitted
20 Apr 2017
Accepted
15 May 2017
First published
15 May 2017

Chem. Commun., 2017,53, 6021-6024

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A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes

L. Song, F. Huang, L. Guo, M. Ouyang and R. Tong, Chem. Commun., 2017, 53, 6021 DOI: 10.1039/C7CC03037A

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