Difluorinated analogues of shikimic acid

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 {Ph 2S[OC(CF 3) 2Ph] 2} was the reagent of choice for the...

Full description

Saved in:

Bibliographic Details
Published in:	Tetrahedron Vol. 59; no. 26; pp. 4827 - 4841
Main Authors:	Begum, Lovely, Box, Julian M, Drew, Michael G.B, Harwood, Laurence M, Humphreys, Jane L, Lowes, David J, Morris, Gareth A, Redon, Perrine M, Walker, Francine M, Whitehead, Roger C
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 23-06-2003
Subjects:	fluorinated analogues Martin's sulfurane shikimic acid Martin's sulfurane shikimic acid fluorinated analogues
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	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 {Ph 2S[OC(CF 3) 2Ph] 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. Graphic
ISSN:	0040-4020 1464-5416
DOI:	10.1016/S0040-4020(03)00697-5