Asymmetric synthesis of conformationally constrained 4-hydroxyprolines and their applications to the formal synthesis of (+)-epibatidine

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  3. Fernández-Recio, M.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

Journal:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Year of publication: 1999

Volume: 10

Issue: 20

Pages: 3999-4007

Type: Article

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DOI: 10.1016/S0957-4166(99)00408-5 SCOPUS: 2-s2.0-0033457356 WoS: WOS:000083745300019 GOOGLE SCHOLAR

More publications in: Tetrahedron: Asymmetry

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Abstract

This report describes the synthesis of enantiomerically pure (1S,3S,4R)- and (1S,3R,4R)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, two new conformationally constrained 4-hydroxyprolines, using a straightforward synthetic route and starting from (-)-8-phenylmenthyl 2-acetamidoacrylate. The easy transformation of the pure (1S,3S,4R)-3-hydroxy-7- azabicyclo[2.2.1]heptane-1-carboxylic acid into (1R,4S)-N-Boc-7- azabicyclo[2.2.1]heptan-2-one constitutes a new formal synthesis of (+)- epibatidine.