In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid

L  Blackburn; H  Kanno; R J K  Taylor

In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid

L Blackburn, H Kanno, R J K Taylor

Chemistry

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

Abstract

Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding alpha,beta-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is also described, in particular as part of a new route to analogues of the arachidonic acid metabolite 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	115-118
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	1
Publication status	Published - 1 Jan 2003

Keywords

MANGANESE-DIOXIDE
5-OXO-ETE

Cite this

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title = "In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid",

abstract = "Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding alpha,beta-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is also described, in particular as part of a new route to analogues of the arachidonic acid metabolite 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "MANGANESE-DIOXIDE, 5-OXO-ETE",

author = "L Blackburn and H Kanno and Taylor, {R J K}",

year = "2003",

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language = "English",

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pages = "115--118",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid

AU - Blackburn, L

AU - Kanno, H

AU - Taylor, R J K

PY - 2003/1/1

Y1 - 2003/1/1

N2 - Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding alpha,beta-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is also described, in particular as part of a new route to analogues of the arachidonic acid metabolite 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

AB - Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding alpha,beta-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is also described, in particular as part of a new route to analogues of the arachidonic acid metabolite 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

KW - MANGANESE-DIOXIDE

KW - 5-OXO-ETE

M3 - Article

SN - 0040-4039

VL - 44

SP - 115

EP - 118

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -