Asymmetric Synthesis of (+)-Hypusine
| Autor: | Brian K. Albrecht, Duane E. DeMong, Robert M. Williams, Rajendra Parasmal Jain |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Hypusine
chemistry.chemical_classification Magnetic Resonance Spectroscopy Molecular Structure Lysine Organic Chemistry Enantioselective synthesis Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Yield (chemistry) Wittig reaction Amino Acid Sequence Physical and Theoretical Chemistry Acetonitrile Lactone |
| Zdroj: | Organic Letters. 3:4287-4289 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol016959o |
| Popis: | 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] |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|