Skip to main content
SpringerLink
Log in

Cyclization of cembrane diterpenoids. VI. Products of the cyclization of 5β-acetoxyisocembrol

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

The structures and the stereochemistries of all the main products of the carbocyclization of 5β-acetoxyisocembrol on its interaction with aqueous formic acid in chloroform have been established. This reaction takes place more selectively than the cyclization of cembrene under the same conditions and is distinguished by the complete predominance in its last stage of the 1,5-hydride shift from C-15 to C-4 over the splitting out of a proton from the C(4)-methyl group.

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

Similar content being viewed by others

References

  1. W. G. Dauben, J. Agr. Food. Chem.,22, 156 (1974).

    Article  CAS  Google Scholar 

  2. W. G. Dauben, J. P. Hubbel, P. Oberhansli, and W. E. Thiessen, J. Org. Chem.,44, 669 (1979).

    Article  CAS  Google Scholar 

  3. V. A. Raldugin, S. A. Shevtsov, and V. A. Pentegova, Izv. Sib. Otd. Akad, Nauk SSSR, Ser. Khim. Nauk, No. 5, 89 (1985).

  4. I. Yu. Bagryanskaya, Yu. V. Gatilov, V. A. Raldugin, S. A. Shevtsov, and V. A. Pentegova, Izv. Sib. Otd. Akad, Nauk SSSR, Ser. Khim. Nauk, No. 5, 94 (1985).

  5. V. A. Raldugin, S. A. Shevtsov, B. I. Mamatyuk, and V. A. Pentegova, Izv. Sib. Otd. Akad, Nauk SSSR, Ser. Khim. Nauk, No. 1, 98 (1986).

  6. A. V. Vorob'ev, G. E. Sal'nikov, M. M. Shakirov, and V. A. Raldugin, Khim. Prir. Soedin., 445 (1991).

  7. M. G. B. Drew, D. H. Templeton, and A. Zalkin, Acta Crystallogr.,25B, 261 (1969).

    Article  CAS  Google Scholar 

  8. V. A. Raldugin, S. A. Shevtsov, Yu. V. Gatilov, I. Yu. Bagryanskaya, and N. I. Yaroshenko, Khim. Prir. Soedin., 687 (1993).

  9. V. A. Raldugin, A. I. Rezvukhin, L. Ya. Korotkikh, and V. A. Pentegova, Khim. Prir. Soedin., 54 (1977).

  10. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 51 (1987).

    Google Scholar 

  11. N. S. Bhacca and D. H. Williams, Applications of NMR Spectroscopy in Organic Chemistry, Holden-Day, San Francico (1964) [Russian translation], Mir, Moscow (1966), p. 150.

    Google Scholar 

  12. C. A. G. Hasnoot, F. A. A. M. de Leeuw, and C. Altona, Tetrahedron,36, 2783 (1980).

    Article  Google Scholar 

  13. P. Crews and E. Kho-Wiseman, J. Org. Chem.,42, 5479 (1977).

    Google Scholar 

Download references

Authors
  1. A. V. Shaptov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Raldugin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. V. Gatilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. Yu. Bagryanskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. M. Shakirov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 249–260, March–April, 1994.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaptov, A.V., Raldugin, V.A., Gatilov, Y.V. et al. Cyclization of cembrane diterpenoids. VI. Products of the cyclization of 5β-acetoxyisocembrol. Chem Nat Compd 30, 229–237 (1994). https://doi.org/10.1007/BF00630012

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00630012

Keywords

Search

Navigation