Metal-catalysed radical cyclisations leading to N-heterocycles: new approaches to gabapentin and pulchellalactam

J S  Bryans; N E A  Chessum; N  Huther; A F  Parsons; F  Ghelfi

doi:10.1016/S0040-4020(03)0103005

Metal-catalysed radical cyclisations leading to N-heterocycles: new approaches to gabapentin and pulchellalactam

J S Bryans, N E A Chessum, N Huther, A F Parsons, F Ghelfi

Chemistry

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

Abstract

The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and the biologically active natural product pulchellalactam. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6221-6231
Number of pages	11
Journal	Tetrahedron
Volume	59
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4020(03)0103005
Publication status	Published - 11 Aug 2003

Keywords

amino acids cyclisations
nitrogen heterocycles
radical reactions
TYROSINE-PHOSPHATASE INHIBITOR
GAMMA-LACTAMS
BETA-LACTAMS
COPPER(I)
ACID
N,N-DIALKYLHYDRAZONES
REARRANGEMENT
ELABORATION
VERSATILE
REAGENT

Access to Document

10.1016/S0040-4020(03)0103005

Cite this

@article{3422c9708e4849fc8d2aaafeef3c027a,

title = "Metal-catalysed radical cyclisations leading to N-heterocycles: new approaches to gabapentin and pulchellalactam",

abstract = "The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and the biologically active natural product pulchellalactam. (C) 2003 Elsevier Ltd. All rights reserved.",

keywords = "amino acids cyclisations, nitrogen heterocycles, radical reactions, TYROSINE-PHOSPHATASE INHIBITOR, GAMMA-LACTAMS, BETA-LACTAMS, COPPER(I), ACID, N,N-DIALKYLHYDRAZONES, REARRANGEMENT, ELABORATION, VERSATILE, REAGENT",

author = "Bryans, {J S} and Chessum, {N E A} and N Huther and Parsons, {A F} and F Ghelfi",

year = "2003",

month = aug,

day = "11",

doi = "10.1016/S0040-4020(03)0103005",

language = "English",

volume = "59",

pages = "6221--6231",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "33",

}

TY - JOUR

T1 - Metal-catalysed radical cyclisations leading to N-heterocycles: new approaches to gabapentin and pulchellalactam

AU - Bryans, J S

AU - Chessum, N E A

AU - Huther, N

AU - Parsons, A F

AU - Ghelfi, F

PY - 2003/8/11

Y1 - 2003/8/11

N2 - The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and the biologically active natural product pulchellalactam. (C) 2003 Elsevier Ltd. All rights reserved.

AB - The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and the biologically active natural product pulchellalactam. (C) 2003 Elsevier Ltd. All rights reserved.

KW - amino acids cyclisations

KW - nitrogen heterocycles

KW - radical reactions

KW - TYROSINE-PHOSPHATASE INHIBITOR

KW - GAMMA-LACTAMS

KW - BETA-LACTAMS

KW - COPPER(I)

KW - ACID

KW - N,N-DIALKYLHYDRAZONES

KW - REARRANGEMENT

KW - ELABORATION

KW - VERSATILE

KW - REAGENT

U2 - 10.1016/S0040-4020(03)0103005

DO - 10.1016/S0040-4020(03)0103005

M3 - Article

SN - 0040-4020

VL - 59

SP - 6221

EP - 6231

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -