Skip to main content
Log in

3-Substituted 1-vinyl-1-methylcyclohex-3-enes — Precursors of tricyclic diterpenoids of the pimarane/rosane group

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

The synthesis of 1-vinyl-1-methyl-3-chloromethylcyclohex-3-ene from 3-vinyl-3-methylcyclohexanone and the corresponding exomethylene derivative has been optimized and related allylsulfones prepared. By a standard combination of these compounds with the appropriate (cyclo)geranyl block synthones a series of regular functionalized diterpenoids has been prepared which are considered as likely precursors of the natural compounds indicated in the title.

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

Literature cited

  1. V. V. Veselovskii (Veselovsky), V. A. Dragan, and A. M. Moiseenkov, Tetrahedron Lett.,31, No. 8, 1187 (1990); A. M. Moiseenkov, V. V. Veselovskii, V. A. Dragan, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1368 (1990); A. M. Moiseenkov, V. A. Dragan, V. V. Veselovskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1361 (1990).

    Google Scholar 

  2. R. M. Coates, Prog. Chem. Org. Nat. Prod.,33, 74 (1976); P. F. Vlad, Izv. Akad. Nauk Mold SSR, Ser. Biol. Khim. Nauk, No. 1, 67 (1977); D. E. Cane, Tetrahedron,36, No. 9, 1109 (1980).

    Google Scholar 

  3. T. McCreadie and K. H. Overton, J. Chem. Soc. (C), No. 2, 312 (1971).

    Google Scholar 

  4. J. W. ApSimon, S. Badripersaund, J. W. Hooper, et al., Can. J. Chem.,56, No. 16, 2139 (1978).

    Google Scholar 

  5. E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc.,87, No. 6, 1353 (1965).

    Google Scholar 

  6. A. M. Moiseenkov, V. A. Dragan, V. A. Koptenkova, and V. V. Veselovskii (Veselovsky), Synthesis, No. 9, 814 (1987); V. V. Veselovskii, V. A. Dragan, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR. Ser. Khim., No. 12, 2787 (1987).

    Google Scholar 

  7. R. M. Coates and H.-Y. Kang, J. Chem. Soc., Chem. Commun., No. 4, 232 (1987).

    Google Scholar 

  8. A. M. Moiseenkov and E. V. Polunin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1368 (1983); M. A. Novikova, A. V. Lozanova, V. V. Veselovskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 356 (1987).

    Google Scholar 

  9. R. V. M. Campbell, L. Crombie, D. A. R. Findley, et al., J. Chem. Soc., Perkin Trans. 1, No. 10, 897 (1975).

    Google Scholar 

  10. M. Stoll, P. Bolle, and L. Ruzicka, Helv. Chim. Acta,33, No. 6, 1510 (1950).

    Google Scholar 

  11. T. Norin and L. Westfelt, Acta Chem. Scand.,17, 1828 (1963).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 857–862, April, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dragan, V.A., Veselovskii, V.V., Daeva, E.D. et al. 3-Substituted 1-vinyl-1-methylcyclohex-3-enes — Precursors of tricyclic diterpenoids of the pimarane/rosane group. Russ Chem Bull 40, 754–759 (1991). https://doi.org/10.1007/BF00958567

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00958567

Keywords

Navigation