A concise route to (+)-lactacystin.
A facile chromatography-free route to Kang's intermediate for the synthesis of (+)-lactacystin, a potent proteasome inhibitor, has been developed starting with Brown's asymmetric crotylation of tert-butyl 5-formyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate, easily available from 2-amino-2-(hydroxymethyl)propane-1,3-diol (Tris).
Ooi
Hidenori
H
Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
Ishibashi
Norihisa
N
Iwabuchi
Yoshiharu
Y
Ishihara
Jun
J
Hatakeyama
Susumi
S
D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002219:Carbamates / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D061988:Proteasome Inhibitors; D013237:Stereoisomerism; D014325:Tromethamine / Q000737:chemistry*
D002219:Carbamates; D061988:Proteasome Inhibitors; D014325:Tromethamine; C067713:lactacystin; D000111:Acetylcysteine