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

被引：17

作者：

Foot, JS

Giblin, GMP

Whitwood, AC

Taylor, RJK ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] GlaxoSmithKline, Dept Med Chem Neurol, Harlow CM19 5AW, Essex, England

[3] GlaxoSmithKline, GI CEDD, Harlow CM19 5AW, Essex, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 05期

关键词：

D O I：

10.1039/b418426b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-Backlund 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.

引用

页码：756 / 763

页数：8