Skip to main content
SpringerLink
Log in

Natural product chemistry, part 137: Oxidation of acridone alkaloids: Synthesis of 5-methoxyacronycine

Naturstoffchemie, 137. Mitt.: Oxidierung von Acridonalkaloiden: Synthese des 5-Methoxyacronycins (Kurze Mitt.)

Short communication

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

Summary

Epoxidation of the acridone alkaloid acronycine (1) resulted in hydroxylation at the aromatic ring giving 5-hydroxyacronycine (3). The same reaction on 1,3-dimethoxy-10-methyl-9(10H)-acridinone (5) gave 1,3-dimethoxy-2-hydroxy-10-methyl-9(10H)-acridinone (6), 1,3-dimethoxy-2-hydroxy-4-peroxy-10-methyl-9(10H)-acridinone (8), and 1,3-dimethoxy-2,4-diperoxy-10-methyl-9(10H)-acridinone (9).

Zusammenfassung

Die Epoxidierung des Acridonalkaloids Acronycin führte zu einer Hydroxylierung des aromatischen Rings, wobei 5-Hydroxyacronycin (3) entstand. Die gleiche Reaktion mit 1,3-Dimethoxy-10-methyl-9(10H)acridinon (5) ergab 1,3-Dimethoxy-2-hydroxy-10-methyl-9(10H)acridinon (6), 1,3-Dimethoxy-2-hydroxy-4-peroxy-10-methyl-9(10H)acridinon (8) und 1,3-Dimethoxy-2,4-diperoxy-10-methyl-9(10H)acridinon (9).

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Part 136: Reisch J., Wickramasinghe A., Probst W. (in press) Monatsh. Chem.

  2. Wickramasinghe A.: A part of the Ph.D. Thesis. Münster

  3. Svoboda G. H. (1966) Lloydia29: 206

    Google Scholar 

  4. Brum-Bousquet M., Tillequin F., Koch M., Sévent T. (1985) Planta Med.51: 536

    Google Scholar 

  5. Svoboda G. H., Poore G. A., Simpson P. J., Boder G. B. (1966) J. Pharm. Sci.55: 758

    Google Scholar 

  6. Suffness M., Cordell G. A. (1985) In: Brossi A. (ed.) The Alkaloids, Vol. 25. Academic Press, New York, pp. 38–48

    Google Scholar 

  7. Brum-Bousquet M., Mitaku S., Skaltsounis A. L., Tillequin F., Koch M. (1988) Planta Med.54: 470

    Google Scholar 

  8. Imuta M., Ziffer H. (1979) J. Org. Chem.44: 1351

    Google Scholar 

  9. Jerina D., Daly J., Witkop B. (1968) J. Am. Chem. Soc.90: 6523

    Google Scholar 

  10. Hughes G. K., Neill K. G., Ritchie E. (1950) Aust. J. Chem.3 A: 497

    Google Scholar 

  11. Ahond A., Picot F., Potier P., Poupat C., Sevenet J. (1978) Phytochemistry17: 166

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Westfälische Wilhelms-Universität, D-4400, Münster, Germany

    Johannes Reisch & Anura Wickramasinghe

Authors
  1. Johannes Reisch
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anura Wickramasinghe
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Reisch, J., Wickramasinghe, A. Natural product chemistry, part 137: Oxidation of acridone alkaloids: Synthesis of 5-methoxyacronycine. Monatsh Chem 121, 709–712 (1990). https://doi.org/10.1007/BF00809777

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00809777

Keywords

Search

Navigation