The synthesis of 6,6-difluoroshikimic acid

Jane L. Humphreys; David J. Lowes; Karen A. Wesson; Roger C. Whitehead

doi:10.1016/j.tetlet.2004.03.033

The synthesis of 6,6-difluoroshikimic acid

Jane L. Humphreys, David J. Lowes, Karen A. Wesson, Roger C. Whitehead

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

Abstract

The synthesis of 6,6-difluoroshikimic acid (4) has been achieved in nine steps from the enantiopure diol 9, which is derived from microbial dihydroxylation of iodobenzene. The synthetic strategy has also been demonstrated to be applicable to the preparation of other 6-substituted analogues of shikimic acid. © 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3429-3432
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2004.03.033
Publication status	Published - 19 Apr 2004

Keywords

Asymmetric synthesis and induction (synthesis of 6,6-difluoroshikimic acid from an asym. diol using an arom. Finkelstein halogen exchange reaction); Halogenation (transhalogenation; synthesis of 6,6-difluoroshikimic acid from an asym. diol using an arom. Finkelstein halogen exchange reaction)

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10.1016/j.tetlet.2004.03.033

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title = "The synthesis of 6,6-difluoroshikimic acid",

abstract = "The synthesis of 6,6-difluoroshikimic acid (4) has been achieved in nine steps from the enantiopure diol 9, which is derived from microbial dihydroxylation of iodobenzene. The synthetic strategy has also been demonstrated to be applicable to the preparation of other 6-substituted analogues of shikimic acid. {\textcopyright} 2004 Elsevier Ltd. All rights reserved.",

keywords = "Asymmetric synthesis and induction (synthesis of 6,6-difluoroshikimic acid from an asym. diol using an arom. Finkelstein halogen exchange reaction); Halogenation (transhalogenation; synthesis of 6,6-difluoroshikimic acid from an asym. diol using an arom. Finkelstein halogen exchange reaction)",

author = "Humphreys, {Jane L.} and Lowes, {David J.} and Wesson, {Karen A.} and Whitehead, {Roger C.}",

year = "2004",

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doi = "10.1016/j.tetlet.2004.03.033",

language = "English",

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T1 - The synthesis of 6,6-difluoroshikimic acid

AU - Humphreys, Jane L.

AU - Lowes, David J.

AU - Wesson, Karen A.

AU - Whitehead, Roger C.

PY - 2004/4/19

Y1 - 2004/4/19

N2 - The synthesis of 6,6-difluoroshikimic acid (4) has been achieved in nine steps from the enantiopure diol 9, which is derived from microbial dihydroxylation of iodobenzene. The synthetic strategy has also been demonstrated to be applicable to the preparation of other 6-substituted analogues of shikimic acid. © 2004 Elsevier Ltd. All rights reserved.

AB - The synthesis of 6,6-difluoroshikimic acid (4) has been achieved in nine steps from the enantiopure diol 9, which is derived from microbial dihydroxylation of iodobenzene. The synthetic strategy has also been demonstrated to be applicable to the preparation of other 6-substituted analogues of shikimic acid. © 2004 Elsevier Ltd. All rights reserved.

KW - Asymmetric synthesis and induction (synthesis of 6,6-difluoroshikimic acid from an asym. diol using an arom. Finkelstein halogen exchange reaction); Halogenation (transhalogenation; synthesis of 6,6-difluoroshikimic acid from an asym. diol using an arom.

U2 - 10.1016/j.tetlet.2004.03.033

DO - 10.1016/j.tetlet.2004.03.033

M3 - Article

SN - 1873-3581

VL - 45

SP - 3429

EP - 3432

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

The synthesis of 6,6-difluoroshikimic acid

Abstract

Keywords

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