SIMPLE HETEROCYCLE, 2-OXAZOLONE, AS VERSATILE BUILDING-BLOCK FOR 2-AMINO ALCOHOLS - CHIRAL SYNTHESIS OF POLYHALOTHREONINES

Authors
ISHIZUKA T OSAKI M ISHIHARA H KUNIEDA T
Citation
T. Ishizuka et al., SIMPLE HETEROCYCLE, 2-OXAZOLONE, AS VERSATILE BUILDING-BLOCK FOR 2-AMINO ALCOHOLS - CHIRAL SYNTHESIS OF POLYHALOTHREONINES, Heterocycles, 35(2), 1993, pp. 901-908
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
35
Issue
2
Year of publication
1993
Pages
901 - 908
Database
ISI
SICI code
0385-5414(1993)35:2<901:SH2AVB>2.0.ZU;2-J
Abstract
Smooth radical-initiated addition of CCl4 and CCl3Br to 3-[(1S)-ketopi nyl]-2-oxazolone gives a 1 : 1 mixture of readily separable (4S, 5R)- and (4R, 5S)-4-halogeno-5-trichloromethyl-2-oxazolidinone derivatives, which serve for facile preparation of polychlorothreonines including 4,4-dichloro-2-amino-3-hydroxybutyric acid, known as antimicrobial arm entomycin analog.