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.
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.
Foot
Jonathan S
JS
Department of Chemistry, University of York, Heslington, York, UKYO10 5DD.
Giblin
Gerard M P
GM
Whitwood
A C
AC
Taylor
R J K
RJ
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*
D000475:Alkenes; D019428:HIV Integrase Inhibitors; D013267:Stilbenes; D013450:Sulfones