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Herstellung von 6,14-Ethenomorphinan-Derivaten

Preparation of 6,14-ethenomorphinan derivatives

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Zusammenfassung

Dihydronorthevinon (2b) wurde aus Dihydrothevinon (2a) mit Azodicarbonsäurediethylester (DEAD) hergestellt und zu einigen neuen N-substituierten Dihydronorthevinon-Derivaten (2c–2g) umgesetzt. Es wurdenGrignard-Reaktionen dieser Verbindungen mit Methylmagnesiumiodid bzw.tert-Butylmagnesiumchlorid durchgeführt. O-Demethylierungen von3a–3j ergaben die entsprechenden N-substituierten Buprenorphin- bzw. Diprenorphin-Analoga4a–4j.

Summary

Dihydronorthevinone (2b) was prepared from dihydrothevinone (2a) with diethyl azodicarboxylate (DEAD) and transformed into a number of new N-substituted dihydronorthevinone derivatives (2c–2g).Grignard reactions of the new compounds with methylmagnesium iodide andtert-butyl-magnesium chloride were studied. O-Demethylation of3a–3j resulted in the corresponding N-substituted buprenorphine and diprenorphine analogs4a–4j.

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Authors and Affiliations

  1. Alkaloida Chemische Werke AG, H-4440, Tiszavasvári, Ungarn

    J. Marton, S. Hosztafi & C. Simon

  2. Lehrstuhl für Organische Chemie der Lajos Kossuth Universität, H-4010, Debrecen, Ungarn

    S. Berényi & S. Makleit

Authors
  1. J. Marton
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  2. S. Hosztafi
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  3. S. Berényi
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  4. C. Simon
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  5. S. Makleit
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Marton, J., Hosztafi, S., Berényi, S. et al. Herstellung von 6,14-Ethenomorphinan-Derivaten. Monatsh Chem 125, 1229–1239 (1994). https://doi.org/10.1007/BF00813809

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  • DOI: https://doi.org/10.1007/BF00813809

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