Skip to main content
Log in

Studies on annelation of (+)-2-caranone

Untersuchungen über die Annelierung von (+)-2-Karanon

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

Summary

The Michael reaction of (+)-2-caranone (1) with methyl vinyl ketone, ethyl vinyl ketone or methyl acrylate was utilized for synthesis of corresponding diketones4 and5 and keto ester8. These compounds were subjected to cyclization to obtain the sesquiterpenoid systems.

Zusammenfassung

Die Michaelreaktion von (+)-2-Karanon mit Methylvinylketon, Ethylvinylketon oder Methylakrylat wurde zur Synthese der entsprechenden Diketone4 und5 und des Ketoesters8 genutzt. Diese Verbindungen wurden weiterhin einer Zyklisierung unterworfen, um zu Sesquiterpenoidstrukturen zu gelangen.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Baeyer A. (1894) Ber.27: 1915

    Google Scholar 

  2. Bates R. B., Buchi G., Matssura T., Shaffer R. R. (1960) J. Am. Chem. Soc.82: 2327

    Google Scholar 

  3. Caine D., Gupton J. T. (1974) J. Org. Chem.39: 2654

    Google Scholar 

  4. Kutney J. P., Balsevich J., Grice P. (1980) Can. J. Chem.58: 2641

    Google Scholar 

  5. Spencer T. A., Neel H. S., Flechtner T. W., Zayle R. A. (1965) Tetrahedron Lett.43: 3889

    Google Scholar 

  6. Głowiak T., Hebda C., Szykuła J. (1989) J. Crystallogr. Spectrosc. Res.19: 167

    Google Scholar 

  7. Ho T.-L. (1988) Carbocycle Construction in Terpene Synthesis. VCH, New York, pp. 5, 150

    Google Scholar 

  8. Malhotra S. K., Johnson F. (1965) Tetrahedron Lett.45: 4027

    Google Scholar 

  9. Fujimoto G. I. (1951) J. Am. Chem. Soc.73: 1856

    Google Scholar 

  10. Belleau B. (1951) J. Am. Chem. Soc.73: 5441

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hebda, C., Szykula, J., Orpiszewski, J. et al. Studies on annelation of (+)-2-caranone. Monatsh Chem 122, 1029–1034 (1991). https://doi.org/10.1007/BF00811111

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00811111

Keywords

Navigation