Reaktionsgleichung
C12C[CH:4](C=C1)[C:3](=[O:8])N2.Cl.[NH2:10][C@@H:11]1[CH2:15][C@H:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12]1.[CH3:19]O>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:3]([NH:10][C@@H:11]1[CH2:15][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12]1)(=[O:8])[CH3:4]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The recent description of an unequivocal route to 2-azabicyclo[2.2.1]hept-5-en-3-one (1, referring to the corresponding number on the flow sheet) (Jagt et al, J. Org. Chem., 39, 564 (1974)) offers a unique starting point for the synthesis of carbocyclic aminonucleosides of known geometric configuration. Acidic hydrolysis of this compound to cis-4-aminocyclopent-2-ene carboxylic acid hydrochloride, followed by esterification of the carboxyl function in refluxing methanol and subsequent acetylation of the amino group in acetic anhydride-pyridine, gives methyl(+)-cis-4-acetamidocyclopent-2-ene carboxylate (2). Reduction of the methyl ester of 2 gives, after acetylation, acetate 3. Epoxidation of acetate 3 is stereoselective due to the syn-directing allylic amide group, giving only the cis-epoxide 4. Hydrolysis of the easily synthesized epoxide 4 and subsequent acetylation gives a mixture of 5, 6 and 6a.
Quellen und Nachweise
- ORD-Eintrag
- ord-bb7975da3d4749b1ad04c068f8fc9516
- Quelldatensatz
- uspto-grants-1980_09
- Patentnummer
- US04223156
Verknüpfte Notizen
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