Synthesis of new conformationally rigid phenylalanine analogues
- Cativiela, C. 2
- Díaz-de-Villegas, M.D. 2
- Avenoza, A. 1
- Peregrina, J.M. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0040-4020
Datum der Publikation: 1993
Ausgabe: 49
Nummer: 47
Seiten: 10987-10996
Art: Artikel
Andere Publikationen in: Tetrahedron
Zusammenfassung
The reactivity of (Z)-2-phenyl-4-benzylidene-5(4H)-oxazolone 1 as dienophile in the Diels-Alder reaction with 1,3-butadiene and 2,3-dimethyl-1,3-butadiene is studied. The adducts obtained starting from the cycloaddition of 1 with both dienes are converted, through simple reactions, into the conformationally restricted cyclic amino acids cis-1-amino-2-phenylcyclohexanecarboxylic acid 6 and 1-amino-c-4,c-5-dimethyl-t-2-phenyl-r-1-cyclohexanecarboxylic acid 10, analogues of phenylalanine.