Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors

  1. Pérez-Fernández, M. 1
  2. Avenoza, A. 1
  3. Busto, J.H. 1
  4. Peregrina, J.M. 1
  5. Rodríguez, F. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Journal:
ARKIVOC

ISSN: 1551-7004

Year of publication: 2010

Volume: 2010

Issue: 3

Pages: 191-202

Type: Article

DOI: 10.3998/ARK.5550190.0011.317 SCOPUS: 2-s2.0-77953441235 WoS: WOS:000273559700017 GOOGLE SCHOLAR lock_openDigital CSIC editor

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Abstract

The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael and Wittig-like reactions, providing some evidence of the mechanism proposed.