title: Practical synthesis of a key intermediate for lactacystin from (R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate.
abstract: A practical synthesis of a key intermediate for the proteasome inhibitor lactacystin from (R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate was established. (R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate is a useful chiral building block for the synthesis of biologically active compounds containing alpha-substituted alpha-amino acid moieties.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo, Japan. miyaaokah@ps.toyaku.ac.jp
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Miyaoka
authors.forename: Makoto
authors.initials: M
authors.lastname: Yamanishi
authors.forename: Ayako
authors.initials: A
authors.lastname: Hoshino
authors.forename: Hidemichi
authors.initials: H
authors.lastname: Mitome
authors.forename: Etsuko
authors.initials: E
authors.lastname: Kawashima
mesh_terms: D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002851:Chromatography, High Pressure Liquid; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000138:chemical synthesis*; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
chemical_list: C529730:(R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate; D015853:Cysteine Proteinase Inhibitors; D007202:Indicators and Reagents; D010080:Oxazoles; D012997:Solvents; C067713:lactacystin; D000111:Acetylcysteine