Stereoselective hydroboration of 5-dimethylaminomethyl-2-methyl-4,5-dihydrofuran: A simple way to (±)-muscarine

  • Yu. N. Bubnov
  • M. E. Gurskii
Brief Communications


A fundamentally new scheme was found for the synthesis of (±)-muscarine, in which the required arrangement of all the substituents is achieved in a single step, involving the hydroboration of 5-dimethylaminomethyl-2-methyl-4,5-dihydrofuran.


Single Step Muscarine Dihydrofuran 
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Literature cited

  1. 1.
    K. G. Eigster, “The chemistry of muscarine,” Advances in Organic Chemistry [Russian translation], Vol. 2, Mir, Moscow (1964), p. 430.Google Scholar
  2. 2.
    D. J. Triggle, The Neurotransmitter-Receptor Interaction, Academic Press, New York (1971).Google Scholar
  3. 3.
    T. Matsumoto, A. Ichihara, and N. Ito, Tetrahedron,25, 5889 (1969).Google Scholar
  4. 4.
    R. Amouroux, B. Gerin, and M. Chastrette, Tetrahedron Lett.,23, 4341 (1982).Google Scholar
  5. 5.
    E. Hardegger and F. Lohse, Helv. Chim. Acta,40, 2383 (1957).Google Scholar
  6. 6.
    J. Whiting, Y.-K. Au-Young, B. Belleau, Can. J. Chem.,50, 3322 (1972).Google Scholar
  7. 7.
    S. Pochet and T. Huynh-Dinh, J. Org, Chem.,47, 193 (1982).Google Scholar
  8. 8.
    R. Amouroux, B. Gerin, and M. Chastrette, Tetrahedron,41, 5321 (1985).Google Scholar
  9. 9.
    A. Bandzouzi and Y. Chapleur, J. Chem. Soc., Perkin Trans, 1, 661 (1987).Google Scholar
  10. 10.
    B. M. Mikhailov and Yu. N. Bubnov, Organoboron Compounds in Organic Synthesis [in Russian], Nauka, Moscow (1977), p. 63.Google Scholar
  11. 11.
    H. C. Brown and G. Zweifel, J. Am. Chem. Soc.,83, 2544 (1961).Google Scholar
  12. 12.
    G. Zweifel and J. Plamondon, J. Org. Chem.,35, 898 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • Yu. N. Bubnov
    • 1
  • M. E. Gurskii
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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