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; Gerard M. P. Giblin; A. C. Whitwood; R. J. K. Taylor

doi:10.1039/B418426B

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Organic & Biomolecular Chemistry

Issue 5, 2005

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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

Jonathan S. Foot , Gerard M. P. Giblin , A. C. Whitwood and R. J. K. Taylor

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

DOI: 10.1039/B418426B
Received 08 Dec 2004, Accepted 12 Jan 2005
First published on the web 09 Feb 2005

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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.

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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

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