SpringerLink
Log in

Synthetic transformations of higher terpenoids: XVIII. Synthesis of optically active 9,10-anthraquinone derivatives

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Retro-Diels-Alder decomposition of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones obtained from a tricyclic diterpenoid, levopimaric acid, gave optically active 5-[2-(6-vinyl-2,6-dimethyl-2-carboxycyclohexyl) ethyl]-7-isopropyl-1,4-naphthoquinones which reacted with silyloxybutadienes to produce the corresponding 6- and 7-hydroxyanthraquinones, 5-furyl-7-hydroxytetrahydroanthraquinones, or 5-furyl-7-oxohexahydroanthraquinones. Condensation of the naphthoquinone derivatives with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide resulted in the formation of 6,11-dioxodihydro- and 6,11-dioxohexahydroanthra[2,1-b]thiophene 3,3-dioxides. 6- and 7-Hydroxyanthraquinones were also obtained by reaction of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones with Danishevsky diene, followed by cleavage of the polycyclic adducts. The cycloaddition of 5-[2-(-2-carboxy-2,6-dimethyl-6-vinylcyclohexyl)ethyl]-7-isopropyl-1,4-naphthoquinones in the presence of Lewis acids was characterized by increased regioselectivity.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Kharitonov, Yu.V., Shul’ts, E.E., Shakirov, M.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2008, vol. 44, p. 516.

    Article  CAS  Google Scholar 

  2. Thomson, R.H., Naturally Occurring Quinones IV. Recent Advances, London: Chapman & Hall, 1997, p. 309.

    Google Scholar 

  3. Gorelik, M.V., Khimiya antrakhinonov i ikh proizvodnykh (Chemistry of Anthraquinones and Their Derivatives), Moscow: Khimiya, 1983.

    Google Scholar 

  4. Gauze, G.F.B. and Dudnik, Yu.V., Protivoopukholevye antibiotiki (Antitumor Antibiotics), Moscow: Meditsina, 1987.

    Google Scholar 

  5. Tolstikov, G.A., Shul’ts, E.E., Mukhametzyanova, T.Sh., Baikova, I.P., and Spirikhin, L.V., Zh. Org. Khim., 1993, vol. 29, p. 698.

    CAS  Google Scholar 

  6. Herz, W., Blackstone, R.C., and Nair, M.G., J. Org. Chem., 1967, vol. 32, p. 2992.

    Article  CAS  Google Scholar 

  7. Danishefsky, S., Kitahara, T., Yan, C.F., and Morris, J., J. Am. Chem. Soc., 1979, vol. 101, p. 6996; Brown-bridge, P., Synthesis, 1983, p. 85.

    Article  CAS  Google Scholar 

  8. Tolstikov, G.A., Shul’ts, E.E., Safarova, G.M., Spirikhin, L.V., and Panasenko, A.A., Zh. Org. Khim., 1990, vol. 26, p. 1283.

    CAS  Google Scholar 

  9. Shul’ts, E.E., Petrova, T.N., Rybalova, T.V., Gatilov, Yu.V., and Tolstikov, G.A., Russ. J. Org. Chem., 1998, vol. 34, p. 845.

    CAS  Google Scholar 

  10. Argyle, C.S., Mason, K.G., Smith, M.A., and Stern, E.S., J. Chem. Soc. C, 1967, p. 2176.

  11. Ruzicka, L. and Kaufmann, S., Helv. Chim. Acta, 1941, vol. 24, p. 1425.

    Article  CAS  Google Scholar 

  12. Tret’yakova, E.V., Flekhter, O.B., Galin, F.Z., Shul’ts, E.E., and Tolstikov, G.A., Russ. J. Org. Chem., 2005, vol. 41, p. 828.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    E. E. Shul’ts, D. S. Oleinikov, I. V. Nechepurenko, M. M. Shakirov & G. A. Tolstikov

Authors
  1. E. E. Shul’ts
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. S. Oleinikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. V. Nechepurenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. M. Shakirov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. A. Tolstikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. E. Shul’ts.

Additional information

Original Russian Text © E.E. Shul’ts, D.S. Oleinikov, I.V. Nechepurenko, M.M. Shakirov, G.A. Tolstikov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 1, pp. 108–119.

For communication XVII, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shul’ts, E.E., Oleinikov, D.S., Nechepurenko, I.V. et al. Synthetic transformations of higher terpenoids: XVIII. Synthesis of optically active 9,10-anthraquinone derivatives. Russ J Org Chem 45, 102–114 (2009). https://doi.org/10.1134/S1070428009010138

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009010138

Keywords

Search

Navigation