Issue 5, 2005
From the journal:

Organic & Biomolecular Chemistry

Unexpected Z-stereoselectivity in the Ramberg–Bäcklund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus

Jonathan S. Foot,a   Gerard M. P. Giblin,b   A. C. Whitwooda  and  R. J. K. Taylor*a  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: rjkt1@york.ac.uk
Tel: 01904 432606

b Department of Medicinal Chemistry, Neurology and GI CEDD, GlaxoSmithKline, New Frontiers Science Park North, Harlow, UK

Abstract

With certain substituent patterns, benzyl benzyl sulfone systems have been found to give unexpectedly high Z-stereoselectivity (up to E : Z = 1 : 16) in the Meyers variant of the Ramberg–Bäcklund reaction. A range of sulfones, bearing various aryl substituents, were explored to rationalize this unprecedented selectivity for Z-stilbene systems. This high level of double bond stereocontrol has also been utilized in the synthesis of integrastatin nucleus, the core of two highly bioactive anti-HIV compounds.

Graphical abstract: Unexpected Z-stereoselectivity in the Ramberg–Bäcklund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus

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Article information

DOI
https://doi.org/10.1039/B418426B
Article type
Paper
Submitted
08 Dec 2004
Accepted
12 Jan 2005
First published
09 Feb 2005

Org. Biomol. Chem., 2005,3, 756-763

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Unexpected Z-stereoselectivity in the Ramberg–Bäcklund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus

J. S. Foot, G. M. P. Giblin, A. C. Whitwood and R. J. K. Taylor, Org. Biomol. Chem., 2005, 3, 756 DOI: 10.1039/B418426B

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