Skip to main content
SpringerLink
Log in

Stereoselective synthesis of (±)-indolizidines 167B and 209D and theirtrans-isomers based on the reductive allylboration of pyridine

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A general method for the synthesis of 5-substituted indolizidines based on intramolecular cyclization oftrans- andcis-2-allyl-6-R-1,2,3,6-tetrahydropyridines, obtained from pyridine and triallylborane, has been elaborated. The closure of the five-membered ring is carried out by hydroboration-oxidation followed by cyclization of the resulting δ-amino alcohols in the presence of the Ph3P−CBr4−Et3N system. (Pr2BH)2 and Pr3B are used as the hydroborating reagents, and H2O2 in an acid medium is used for the oxidation of 2-[3-(dipropylboryl]-Δ2-piperideines formed. This method has been used for the synthesis of two natural alkaloids: indolizidine 209D (cis-5-hexylindolizidine) and itstrans-isomer were prepared fromcis- andtrans-2-allyl-6-hexyl-1,2,3,6-tetrahydropiridine, respectively; indolizidine 167B andtrans-5-propylindolizidine were synthesized fromcis- andtrans-2,6-diallyl-1,2,3,6-tetra-hydropyridine, respectively.

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. J. W. Daly and T. F. Spande, inAlkaloids: Chemical and Biological Perspectives, Eds. S. W. Pelletier, Wiley, New York, 1986,4, Ch. 1, 1; (b) H. Takahata and T. Motose, inThe Alkaloids, Ed. G. A. Cordell, Academic Press, New York, 1993,44, 189.

    Google Scholar 

  2. R. S. Aronstam, J. W. Daly, T. F. Spande, T. K. Narayanan, and E. X. Albuquerque,Neurochem. Res., 1986,d11, 1227.

    Article  Google Scholar 

  3. J. W. Daly,Fortschr. Chem. Org. Naturst., 1982,41, 205.

    CAS  Google Scholar 

  4. M. F. Raub, J. H. Cardellina II and T. F. Spande,Tetrahedron Lett., 1992,33, 2257.

    Article  CAS  Google Scholar 

  5. Y. Shishido and Ch. Kibayashi,J. Org. Chem., 1992,57, 2876.

    Article  CAS  Google Scholar 

  6. A. L. Smith, S. F., Williams, A. B. Holmes, L. R. Hughes, Z. Lidert, and C. Swithenbank,J. Org. Chem., 1991,56, 1393.

    Article  Google Scholar 

  7. J. Ahman and P. Somfai,Tetrahedron, 1995,51, 9747; (b) C. W. Jefford and J. B. Wang,Tetrahedron Lett., 1993,34, 3119; (c) R. P. Polniaszek and S. E. Belmont,J. Org. Chem., 1990,55, 4688 (see also the references cited in these papers).

    Article  Google Scholar 

  8. Yu. N. Bubnov, E. V. Klimkina, A. V. Ignatenko, and I. D. Gridnev,Tetrahedron Lett., 1996,37, 1337.

    Article  Google Scholar 

  9. Yu. N. Bubnov, E. V. Klimkina, and A. V. Ignatenko,Izv. Akad. Nauk, Ser. Khim., 1998, 468 [Russ. Chem. Bull., 1998,47, 451 (Engl. Transl.)].

  10. Yu. N. Bubnov, E. V. Klimkina, A. V. Ignatenko, and I. D. Gridnev,Tetrahedron Lett., 1997,38, 4631.

    Article  CAS  Google Scholar 

  11. Yu. N. Bubnov,Pure Appl. Chem., 1994,66, 235; (b) Yu. N. Bubnov, E. A. Shagova, S. V. Evchenko, and A. V. Ignatenko,Izv. Akad. Nauk, Ser. Khim., 1994, 693 [Russ. Chem. Bull., 1994,43, 645 (Engl. Transl.)]; (c) Yu. N. Bubnov,Izv. Akad. Nauk, Ser. Khim., 1995, 1202 [Russ. Chem. Bull., 1995,44, 1156 (Engl. Transl.)].

    CAS  Google Scholar 

  12. B. M. Mikhailov and Yu. N. Bubnov,Bororganicheskie soedineniya v organicheskom, sinteze. [Organoboron Compounds in Organic Synthesis], Nauka, Moscow, 1977, 167 (in Russian); B. M. Mikhailov and Yu. N. Bubnov,Oranoboron Compounds in Organic Synthesis Harwood Acad. Publ., London—New York, 1984.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    Yu. N. Bubnov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation

    E. V. Klimkina & A. V. Ignatenko

Authors
  1. Yu. N. Bubnov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Klimkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Ignatenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 971–979, May, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bubnov, Y.N., Klimkina, E.V. & Ignatenko, A.V. Stereoselective synthesis of (±)-indolizidines 167B and 209D and theirtrans-isomers based on the reductive allylboration of pyridine. Russ Chem Bull 47, 941–949 (1998). https://doi.org/10.1007/BF02498166

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02498166

Key words

Search

Navigation