Issue 20, 2006
From the journal:

Organic & Biomolecular Chemistry

Stereocontrolled synthesis of highly functionalised spirocyclic pyrans†

Stephen J. Hobsona  and  Rodolfo Marquez‡*a  

* Corresponding authors

a WestCHEM, Department of Chemistry, University of Glasgow, Glasgow, UK
E-mail: r.marquez@chem.gla.ac.uk
Fax: +44 (0)141 330 4888
Tel: +44(0)141 330 8491

Abstract

Highly functionalised spirocyclic pyrans can be obtained through the Achmatowicz rearrangement of furyl carbinols by taking advantage of the different rates of reaction for epoxidation and nucleophilic addition. Through this methodology, spirocyclic units of various ring sizes can be selectively generated with complete stereocontrol.

Graphical abstract: Stereocontrolled synthesis of highly functionalised spirocyclic pyrans

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Article information

DOI
https://doi.org/10.1039/B611737F
Article type
Paper
Submitted
14 Aug 2006
Accepted
17 Aug 2006
First published
04 Sep 2006

Org. Biomol. Chem., 2006,4, 3808-3814

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Stereocontrolled synthesis of highly functionalised spirocyclic pyrans

S. J. Hobson and R. Marquez, Org. Biomol. Chem., 2006, 4, 3808 DOI: 10.1039/B611737F

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