New synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids

  1. Avenoza, A. 1
  2. Barriobero, J.I. 1
  3. Cativiela, C. 2
  4. Fernández-Recio, M.A. 1
  5. Peregrina, J.M. 1
  6. Rodríguez, F. 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: 2001

Volumen: 57

Número: 14

Páginas: 2745-2755

Tipo: Artículo

DOI: 10.1016/S0040-4020(01)00129-6 SCOPUS: 2-s2.0-0035794992 WoS: WOS:000167884400009 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

This report describes a new synthesis of the four stereoisomers of 1-amino-2-hydroxycyclohexanecarboxylic acids [(1S,2S)-, (1R,2R)-, (1S,2R)- and (1R,2S)-c 6Ser], four conformationally constrained serine (Ser) analogues, possessing a six-membered carbocyclic ring. Initially, we synthesised cis-c 6Ser and trans-c 6Ser in their racemic forms, using as key steps the Diels-Alder reactions of methyl 2-benzamidoacrylate with Danishefsky's diene and 1-methoxy-1,3-butadiene, respectively. The optically active forms were achieved by resolution methods. © 2001 Elsevier Science Ltd.