Difluorinated analogues of shikimic acid

Lovely Begum; Julian M. Box; Michael G B Drew; Laurence M. Harwood; Jane L. Humphreys; David J. Lowes; Gareth A. Morris; Perrine M. Redon; Francine M. Walker; Roger C. Whitehead

doi:10.1016/S0040-4020(03)00697-5

Difluorinated analogues of shikimic acid

Lovely Begum, Julian M. Box, Michael G B Drew, Laurence M. Harwood, Jane L. Humphreys, David J. Lowes, Gareth A. Morris, Perrine M. Redon, Francine M. Walker, Roger C. Whitehead

Research output: Contribution to journal › Article › peer-review

Abstract

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)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. © 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	4827-4841
Number of pages	14
Journal	Tetrahedron
Volume	59
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4020(03)00697-5
Publication status	Published - 23 Jun 2003

Keywords

Fluorinated analogues
Martin's sulfurane
Shikimic acid

Access to Document

10.1016/S0040-4020(03)00697-5

Cite this

@article{7d2917bd349941b985767929dd75f4ee,

title = "Difluorinated analogues of shikimic acid",

abstract = "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)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. {\textcopyright} 2003 Elsevier Science Ltd. All rights reserved.",

keywords = "Fluorinated analogues, Martin's sulfurane, Shikimic acid",

author = "Lovely Begum and Box, {Julian M.} and Drew, {Michael G B} and Harwood, {Laurence M.} and Humphreys, {Jane L.} and Lowes, {David J.} and Morris, {Gareth A.} and Redon, {Perrine M.} and Walker, {Francine M.} and Whitehead, {Roger C.}",

year = "2003",

month = jun,

day = "23",

doi = "10.1016/S0040-4020(03)00697-5",

language = "English",

volume = "59",

pages = "4827--4841",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier BV",

number = "26",

}

TY - JOUR

T1 - Difluorinated analogues of shikimic acid

AU - Begum, Lovely

AU - Box, Julian M.

AU - Drew, Michael G B

AU - Harwood, Laurence M.

AU - Humphreys, Jane L.

AU - Lowes, David J.

AU - Morris, Gareth A.

AU - Redon, Perrine M.

AU - Walker, Francine M.

AU - Whitehead, Roger C.

PY - 2003/6/23

Y1 - 2003/6/23

N2 - 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)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. © 2003 Elsevier Science Ltd. All rights reserved.

AB - 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)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. © 2003 Elsevier Science Ltd. All rights reserved.

KW - Fluorinated analogues

KW - Martin's sulfurane

KW - Shikimic acid

U2 - 10.1016/S0040-4020(03)00697-5

DO - 10.1016/S0040-4020(03)00697-5

M3 - Article

SN - 0040-4020

VL - 59

SP - 4827

EP - 4841

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

Difluorinated analogues of shikimic acid

Abstract

Keywords

Access to Document

Fingerprint

Cite this