The synthesis of 4-arylsulfanyl-substituted kainoid analogues from trans-4-hydroxy-L-proline

Citation
Je. Baldwin et al., The synthesis of 4-arylsulfanyl-substituted kainoid analogues from trans-4-hydroxy-L-proline, TETRAHEDRON, 57(37), 2001, pp. 7991-7997
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
37
Year of publication
2001
Pages
7991 - 7997
Database
ISI
SICI code
0040-4020(20010910)57:37<7991:TSO4KA>2.0.ZU;2-1
Abstract
The potent neuroexcitatory activity of kainoid amino acids in the mammalian CNS places new analogues in high demand as tools for neuropharmacological research. A range of 4-arylsulfanyl-substituted kainoids has been synthesis ed in a parallel fashion via mesylate displacement by a number of aromatic thiolates upon (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-methanesu lfonyloxypyrrohdine-2-carboxylic acid methyl ester 9, which is obtainable i n eight steps from trans-4-hydroxy-L-proline 5. (C) 2001 Elsevier Science L td. All rights reserved.