Asymmetric synthesis of (+)-hypusine.
Wittig reaction of (triphenylphosphoranylidene)acetonitrile with the lactone carbonyl of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (3) and subsequent reduction generates morpholinylethylamine dihydrochloride (5) in quantitative yield and with excellent diastereoselectivity. Compound 5 was readily converted into hypusine dihydrochloride (1.2HCl) in overall 53% yield. [reaction: see text]
Jain
R P
RP
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Albrecht
B K
BK
DeMong
D E
DE
Williams
R M
RM
D000595:Amino Acid Sequence; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
C100028:hypusine; D008239:Lysine