Skip to main content
SpringerLink
Log in

Stereoselective Synthesis of (7aS)-1-Methylenehexahydro-1H-pyrrolizine and (−)-Heliotridane from N-Diphenylmethyl-(S)-proline Ethyl Ester

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

Abstract

Alkaloid (7aS)-1-methylenehexahydro-1H-pyrrolizine was synthesized from N-diphenylmethyl-(S)-proline ethyl ester by cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium tetraisopropoxide, replacement of the protecting group on the nitrogen atom, and cationic cyclopropylallyl isomerization of (S)-1-(1-ethoxycarbonylpyrrolidin-2-yl)cyclopropyl sulfonate into the corresponding allyl bromide. Stereoselective reduction of (7aS)-1-methylenehexahydro-1H-pyrrolizine with sodium tetrahydridoborate in the presence of nickel chloride afforded (−)-heliotridane [(1S,7aS]-1-methylhexahydro-1H-pyrrolizine] in high yield.

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. Gibson, D.H. and De Puy, C.H., Chem. Rev., 1974, vol. 74, p. 605.

    Article  CAS  Google Scholar 

  2. Kulinkovich, O.G., Chem. Rev., 2003, vol. 103, p. 2597.

    Article  CAS  PubMed  Google Scholar 

  3. Lysenko, I.L. and Kulinkovich, O.G., Russ. J. Org. Chem., 2001, vol. 37, p. 1238.

    Article  CAS  Google Scholar 

  4. Lysenko, I.L., Bekish, A.V., and Kulinkovich, O.G., Russ. J. Org. Chem., 2002, vol. 38, p. 875.

    Article  CAS  Google Scholar 

  5. Kulinkovich, O.G., Sviridov, S.V., and Vasilevskii, D.A., Synthesis, 1991, p. 234.

  6. Culvenor, C.C.J. and Smith, L.W., Aust. J. Chem., 1959, vol. 12, p. 255.

    CAS  Google Scholar 

  7. Culvenor, C.C.J. and Smith, L.W., Aust. J. Chem., 1962, vol. 15, p. 328.

    CAS  Google Scholar 

  8. Honda, T., Yamane, S., Naito, K., and Suzuki, Y., Heterocycles, 1995, vol. 40, p. 301.

    CAS  Google Scholar 

  9. Kochetkov, N.K., Likhosherstov, A.M., and Kritsyn, A.M., Tetrahedron Lett., 1961, p. 92.

  10. Yoshida, K., Nakajima, Sh., Wakamatsu, T., Ban, Y., and Shibasaki, M., Heterocycles, 1988, vol. 27, p. 1167.

    CAS  Google Scholar 

  11. Kozyrkov, Y.Y. and Kulinkovich, O.G., Synlett, 2002, p. 443.

  12. Giovannini, R., Marcantoni, E., and Petrini, M., J. Org. Chem., 1995, vol. 60, p. 5706.

    Article  CAS  Google Scholar 

  13. Toshio, S., Kenrio, N., and Shuichi, S., Chem. Pharm. Bull., 1971,vol. 19, p. 817.

    Google Scholar 

  14. Burnett, D.A., Choi, J.-K., and Hart, D.J., J. Am. Chem. Soc., 1984, vol. 106, p. 8201.

    Article  CAS  Google Scholar 

  15. Garst, M.E., Bonfiglio, J.N., and Marks, J., J. Org. Chem., 1982, vol. 47, p. 1494.

    Article  CAS  Google Scholar 

  16. Culvenor, C.C.J. and Smith, L.W., Aust. J. Chem., 1962, vol. 15, p. 121.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Belarussian State University, pr. Skoriny 4, Minsk, 220050, Belarus

    I. L. Lysenko & O. G. Kulinkovich

Authors
  1. I. L. Lysenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. G. Kulinkovich
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 73–77.

Original Russian Text Copyright © 2005 by Lysenko, Kulinkovich.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lysenko, I.L., Kulinkovich, O.G. Stereoselective Synthesis of (7aS)-1-Methylenehexahydro-1H-pyrrolizine and (−)-Heliotridane from N-Diphenylmethyl-(S)-proline Ethyl Ester. Russ J Org Chem 41, 70–74 (2005). https://doi.org/10.1007/s11178-005-0123-0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0123-0

Keywords

Search

Navigation