Synthesis of Functionalized Pyrrolidin-2-ones and (S)-Vigabatrin from Pyrrole

Starting from pyrrole, the novel 3,4-didehydropyrohomoglutamate 8 or (ent)-8 can be efficiently synthesized in up to 91% ee, which can be utilized as a versatile building block toward functionalized pyrrolidin-2-ones. Moreover, (ent)-8 can be readily converted to (S)-Vigabatrin, being an irreversibl...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-03, Vol.71 (5), p.2173-2176
Main Authors: Gheorghe, Alexandru, Schulte, Michael, Reiser, Oliver
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Pyrroles - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
Vigabatrin - chemical synthesis
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Summary:Starting from pyrrole, the novel 3,4-didehydropyrohomoglutamate 8 or (ent)-8 can be efficiently synthesized in up to 91% ee, which can be utilized as a versatile building block toward functionalized pyrrolidin-2-ones. Moreover, (ent)-8 can be readily converted to (S)-Vigabatrin, being an irreversible inhibitor for GABA-T, which is used as adjunctive therapy in patients that suffer from epilepsy.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0524472