Issue 37, 2016
From the journal:

RSC Advances

Alkynylation/dearomatizative cyclization to construct spiro[5.5]undecanes†

Jidong Shao,a   Liqi Li,*a   Jie Zhang,b   Jingping Hu,a   Jijun Xuea  and  Ying Li*a  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China
E-mail: liying@lzu.edu.cn, lilq@lzu.edu.cn

b State Key Laboratory of Fluorine & Nitrogen Chemicals, Xi'an Modern Chemistry Research Institute, Xi'an, P. R. China

Abstract

A new access to spiro[5.5]undecane frameworks was reported through the ZnMe2-promoted alkynylation of salicylaldehyde and HCO2H-mediated dearomatizative cyclization which can be used to construct an all-carbon quaternary spirocenter. This method can be applied to the rapid synthesis towards a series of useful motifs of natural products, such as the core of elatol and aphidicolin.

Graphical abstract: Alkynylation/dearomatizative cyclization to construct spiro[5.5]undecanes

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Article information

DOI
https://doi.org/10.1039/C6RA02463G
Article type
Communication
Submitted
27 Jan 2016
Accepted
20 Mar 2016
First published
22 Mar 2016

RSC Adv., 2016,6, 31363-31366

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Alkynylation/dearomatizative cyclization to construct spiro[5.5]undecanes

J. Shao, L. Li, J. Zhang, J. Hu, J. Xue and Y. Li, RSC Adv., 2016, 6, 31363 DOI: 10.1039/C6RA02463G

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