A versatile and stereoselective synthesis of (rac)-epibatidine

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Cativiela, C. 2
  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:
Synthesis (Stuttgart)

ISSN: 0039-7881

Any de publicació: 1998

Volum: 9

Pàgines: 1335-1338

Tipus: Article

SCOPUS: 2-s2.0-0031689769 WoS: WOS:000075952000021 GOOGLE SCHOLAR

Altres publicacions en: Synthesis (Stuttgart)

Resum

A new synthesis of (±)-epibatidine has been achieved, involving a Diels-Alder cycloaddition of (Z)-4-[5'-(2'-chloropyridylmethylene)]-2-phenyl-5(4H)-oxazolone with Danishefsky's diene, and an intramolecular nucleophilic displacement in a trans-1,4-methanesulfonyloxycyclohexylamide derivative as key steps.