Difluorinated analogues of shikimic acid

被引：17

作者：

Begum, L

Box, JM

Drew, MGB

Harwood, LM

Humphreys, JL

Lowes, DJ

Morris, GA

Redon, PM

Walker, FM

Whitehead, RC

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England

来源：

TETRAHEDRON | 2003年 / 59卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

shikimic acid; Martin's sulfurane; fluorinated analogues;

D O I：

10.1016/S0040-4020(03)00697-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4827 / 4841

页数：15

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