Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Über ein 4,5;7,9-Bis-epoxy-hasubanan

A 4,5;7,9-bis-epoxy-hasubanan. Proof of the configuration at C-9 of hydroxy-indolinocodeine derivatives

Beweis für die Konfiguration am C-9 von 9-Hydroxy-indolinocodein-Derivaten

  • 25 Accesses

  • 1 Citations

Abstract

Reaction of the enol ether1 with N-bromoacetamide in methanol gave the 7 β-bromoacetal3 which rearranged in acidic media to the 7,9-epoxide5. As an oxide bridge from C-9 to C-7 in indolinocodeinone can only be formed in the α-position, the isolation of5 is the chemical proof of the configuration at C-9.

This is a preview of subscription content, log in to check access.

Literatur

  1. 1

    W. Fleischhacker undA. Klement, Mh. Chem.107, 1029 (1976).

  2. 2

    W. Fleischhacker undH. Gruber, in Vorbereitung.

  3. 3

    J. Homeyer, J. Org. Chem.21, 370 (1956).

  4. 4

    W. Fleischhacker undA. Klement, Mh. Chem.106, 1513 (1975).

  5. 5

    S. Okuda, S. Yamaguchi, Y. Kawazoe undK. Tsuda, Chem. Pharm. Bull. [Japan]12, 104 (1964).

  6. 6

    T. Rüll, Bull. Soc. Chim. France1963, 586.

  7. 7

    T. Eppenberger, M. Warren undH. Rapoport, Helv. Chim. Acta51, 381 (1968).

  8. 8

    W. Fleischhacker, F. Vieböck undF. Zeidler, Mh. Chem.101, 1215 (1970).

  9. 9

    D. E. Rearick undM. Gates, Tetrahedron Lett.1970, 507.

  10. 10

    W. Fleischhacker undH. Markut, Mh. Chem.102, 643 (1971).

  11. 11

    P. Tsui undG. Just, Canad. J. Chem.21, 3502 (1973).

  12. 12

    S. Okuda, K. Abe undM. Onda, Chem. Pharm. Bull. [Japan]16, 1124 (1968).

  13. 13

    R. M. Allen undG. W. Kirby, Chem. Comm.1970, 1346.

  14. 14

    R. M. Allen undG. W. Kirby, J. Chem. Soc. Perkin I,1973, 363.

Download references

Author information

Correspondence to Doz. Dr. Wilhelm Fleischhacker.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Fleischhacker, W., Klement, A. Über ein 4,5;7,9-Bis-epoxy-hasubanan. Monatshefte für Chemie 108, 953–958 (1977). https://doi.org/10.1007/BF00898059

Download citation