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

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...

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Bibliographic Details
Published in:Tetrahedron 2003-08, Vol.59 (33), p.6221-6231
Main Authors: Bryans, Justin S, Chessum, Nicola E.A, Huther, Nathalie, Parsons, Andrew F, Ghelfi, Franco
Format: Article
Language:English
Subjects:
amino acids
cyclisations
nitrogen heterocycles
radical reactions
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)01030-5