✦ LIBER ✦

Abstracts of Poster Section C; Abstracts of Poster Section D; Abstracts of Poster Section E

Publisher: Wiley (John Wiley & Sons)
Year: 2003
Tongue: English
Weight: 1020 KB
Volume: 71
Category: Article
ISSN: 0006-3525
DOI: 10.1002/bip.10456

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✦ Synopsis

Cyclopentylglycine (Cpg) is a competitive inhibitor of isoleucine uptake in E. coli [1] and also has been used in designing angiotensin II antagonists [2]. We exploited a commercially available chiral auxillary [3] to obtain Cpg. Thus, stereoselective alkylation of the enolate derived from benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (1) with cyclopentyl iodide afforded anti-␣-monosubstituted product, benzyl (2R,3S,5S)-(-)-6-oxo-2,3-diphenyl-5-cyclopentyl-4-morpholinecarboxylate (3) in 60% yield. Catalytic hydrogenolysis over PdCl 2 cleaved the auxiliary ring system to give L-cyclopentylglycine (4) in 84% yield. Subsequent protection of the ␣-amino function with Fmoc-OSu gave Fmoc-L-cyclopentylglycine (5) in high yield.

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