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Asymmetric synthesis of (+)-hypusine
R P Jain1, B K Albrecht, D E DeMong
1Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Organic Letters
|January 11, 2002
Abstract:
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]