Synthesis of new conformationally rigid phenylalanine analogues

  1. Cativiela, C. 2
  2. Díaz-de-Villegas, M.D. 2
  3. Avenoza, A. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Revista:
Tetrahedron

ISSN: 0040-4020

Año de publicación: 1993

Volumen: 49

Número: 47

Páginas: 10987-10996

Tipo: Artículo

DOI: 10.1016/S0040-4020(01)80252-0 SCOPUS: 2-s2.0-0027379951 WoS: WOS:A1993MH25600021 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron

Resumen

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.