A FORMAL STEREOSELECTIVE SYNTHESIS OF A HYDROXYETHYLENE DIPEPTIDE ISOSTERE

Authors
PEYRAT JF CHABOCHE C FIGADERE B CAVE A
Citation
Jf. Peyrat et al., A FORMAL STEREOSELECTIVE SYNTHESIS OF A HYDROXYETHYLENE DIPEPTIDE ISOSTERE, Tetrahedron letters, 36(16), 1995, pp. 2757-2760
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
16
Year of publication
1995
Pages
2757 - 2760
Database
ISI
SICI code
0040-4039(1995)36:16<2757:AFSSOA>2.0.ZU;2-K
Abstract
4-Hydroxy-5-amino-6-phenyl-4-hexanolide has been synthesized under its cyclized form (lactone 5) from a very inexpensive chiral starting mat erial, L-glutamic acid The key steps were an original reduction of car bonyl of a ketone with n-Bu(3)SnH in the presence of silica gel, follo wed by an SN2 displacement of a mesylate group with sodium azide