Skip to main content
SpringerLink
Log in

Dilithiated synthons: synthesis of cyclic ethers

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Recent advances in the generation of dilithiated synthons by arene-catalyzed lithiation of the corresponding dichloro compounds in the presence of carbonyl compounds (Barbier-type reaction conditions) as the key step are described. Further cyclization of the generated diols under different reaction conditions affords a variety of mono-, bi-, and spirocyclic ethers.

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. (a) E. J. Corey and X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989; (b) K. C. Nicolaou and E. J. Sorensen, Classics in Total Synthesis, VCH, Wein-heim, 1996.

  2. Aims and Scope, in Adv. Synth. Catal., Ed. R. Noyori, 2001, 343, A3.

  3. A. Boudier, L. O. Bromm, L. Lotz, and P. Knochel, Angew. Chem., Int. Ed., 2000, 39, 4414.

    Google Scholar 

  4. (a) B. J. Wakefield, Organolithium Methods, Academic Press, London, 1988; (b) Lithium Chemistry. A Theoretical and Experimental Overview, Eds. A.-M. Sapse and P. von Rague Schleyer, Wiley, Chichester, 1995; (c) J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002.

  5. (a) C. Najera and M. Yus, Trends Org. Chem., 1991, 2, 155; (b) C. Najera and M. Yus, Recent Res. Devel. Org. Chem., 1997, 1, 67; (c) M. Yus and F. Foubelo, Rev. Heteroatom Chem., 1997, 17, 73; (d) C. Najera and M. Yus, Curr. Org. Chem., 2003, 7, 867.

  6. M. Yus and D. J. Ramon, J. Chem. Soc., Chem. Commun., 1991, 398.

  7. (a) M. Yus, Chem. Soc. Rev., 1996, 25, 155; (b) D. J. Ramon and M. Yus, Eur. J. Org. Chem., 2000, 225; (c) M. Yus, Synlett, 2001, 1197; (d) M. Yus and D. J. Ramon, Latv. J. Chem., 2002, 79; (e) D. J. Ramon and M. Yus, Rev. Cubana Quim., 2002, 14, 75; (f) M. Yus, in The Chemistry of Organolithium Compounds, Eds. Z. Rappoport and I. Marek, Wiley, Chichester, 2003.

  8. (a) M. Yus, R. P. Herrera, and A. Guijarro, Tetrahedron Lett., 2001, 42, 3455; (b) M. Yus, R. P. Herrera, and A. Guijarro, Chem. Eur. J., 2002, 8, 2574; (c) R. P. Herrera, A. Guijarro, and M. Yus, Tetrahedron Lett., 2003, 44, 1309; (d) R. P. Herrera, A. Guijarro, and M. Yus, Tetrahedron Lett., 2003, 44, 1313.

  9. (a) C. Gomez, S. Ruiz, and M. Yus, Tetrahedron Lett., 1998, 39, 1397; (b) C. Gomez, S. Ruiz, and M. Yus, Tetrahedron, 1999, 55, 7017; (c) M. Yus, C. Gomez, and P. Candela, Tetrahedron, 2002, 58, 6207; (d) T. Arnauld, A. G. M. Barrett, and B. T. Hopkins, Tetrahedron Lett., 2002, 43, 1081.

  10. D. Guijarro and M. Yus, Recent Res. Devel. Org. Chem., 1998, 2, 713.

    Google Scholar 

  11. F. Foubelo and M. Yus, Trends Org. Chem., 1998, 7, 1.

    Google Scholar 

  12. F. Alonso and M. Yus, Recent Res. Devel. Org. Chem., 1997, 1, 397.

    Google Scholar 

  13. F. Alonso, J. Meléndez, and M. Yus Tez. dokl. Memorial´nogo mezhdunar. simp. M. Vol´pina (1923–1996) "Sovremennye napravleniya v metalloorganicheskoi i kataliticheskoi khimii" [Abstrs. M. Vol´pin´s Memorial Intern. Symp. "Modern in Organometallic and Catalytic Chemistry] (Moscow, May 18–23, 2003), Moscow, 2003,-33 (in Russian).

  14. (a) R. B. Bates, B. Gordon, III, P. C. Keller, J. V. Rund, and N. S. Mills, J. Org. Chem., 1980, 45, 168 (and references cited therein); (b) D. Gujarro, B. Mancheno, and M. Yus, Tetrahedron, 1993, 49, 1327.

  15. (a) D. J. Ramon and M. Yus, Tetrahedron Lett., 1992, 33, 2217; (b) C. Gomez, D. J. Ramon, and M. Yus, Tetrahedron, 1993, 49, 4117.

  16. J. G. Buchanan, Prog. Chem. Nat. Org. Prod., 1983, 44, 234.

    Google Scholar 

  17. (a) H. Kizu, N. Sugita, and T. Tomimori, Chem. Pharm. Bull., 1998, 46, 988; (b) M. C. de la Torre, B. Rodriguez, M. Bruno, N. Vassallo, M. L. Bondi, F. Piozzi, and O. Servattaz, J. Nat. Prod., 1997, 60, 1229.

  18. (a) J. Mulzer and J.-T. Mohr, J. Org. Chem., 1994, 59, 1160; (b) J. V. Raman, H. K. Lee, R. Vleggaar, and J. K. Chaa, Tetrahedron Lett., 1995, 36, 3095.

  19. (a) S. Horne, G. Weeratunga, and R. Rodrigo, J. Chem. Soc., Chem. Commun., 1990, 39; (b) G. A. Kraus, B. E. Johnston, and J. M. Applegate, J. Org. Chem., 1991, 56, 5688; (c) M. Koreeda, L. A. Dixon, and J. D. Hsi, Synlett, 1993, 555; (d) E. R. Civitello and H. Rapoport, J. Org. Chem., 1994, 59, 3775; (e) M. C. Pirrung and Y. R. Lee, Tetrahedron Lett., 1996, 37, 2391; (f) T. Bando and K. Shishido, Synlett, 1997, 665.

  20. F. Alonso, E. Lorenzo, and M. Yus, Tetrahedron Lett., 1997, 38, 2187.

    Google Scholar 

  21. E. Lorenzo, F. Alonso, and M. Yus, Tetrahedron, 2000, 56, 1745.

    Google Scholar 

  22. F. Alonso, E. Lorenzo, and M. Yus, Tetrahedron Lett., 1998, 39, 3303.

    Google Scholar 

  23. (a) H. Watanabe, T. Watanabe, and K. Mori, Tetrahedron, 1996, 52, 13939; (b) J. Ishihara, T. Fukuzaki, and A. Murai, Tetrahedron Lett., 1999, 40, 1907; (c) J. Ishihara, Y. Yamamoto, N. Kanoh, and A. Murai, Tetrahedron Lett., 1999, 40, 4387.

  24. R. Aquino, N. De Tomasi, M. Tapia, M. Lauro, and L. Rastrelli, J. Nat. Prod., 1999, 62, 560.

    Google Scholar 

  25. (a) A. Ichihara, M. Nonaka, S. Sakamara, R. Sato, and A. Tajimi, Chem. Lett., 1988, 27; (b) S. R. Graham, J. A. Murphy, and A. R. Kennedy, J. Chem. Soc., Perkin Trans. 1, 1999, 3071.

  26. E. Lorenzo, F. Alonso, and M. Yus, Tetrahedron Lett., 2000, 41, 1661.

    Google Scholar 

  27. G. M. Massanet, I. G. Collado, F. A. Macias, F. Bohlmann, and J. Japukovic, Tetrahedron Lett., 1983, 24, 1644.

    Google Scholar 

  28. (a) I. G. Collado, F. A. Macias, G. M. Massanet, and F. Rodriguez Luis, Phytochemistry, 1985, 24, 2107; (b) I. G. Collado, F. A. Macias, G. M. Massanet, and F. Rodriguez Luis, Tetrahedron, 1986, 42, 3611.

  29. F. Alonso, L. R. Falvello, P. E. Fanwick, E. Lorenzo, and M. Yus, Synthesis, 2000, 949.

  30. D. Seebach, Angew. Chem., Int. Ed. Engl., 1979, 18, 239.

    Google Scholar 

  31. (a) M. Schlosser and V. Ladenberger, Angew. Chem., Int. Ed. Engl., 1966, 5, 519; (b) C. G. Screttas and M. Micha-Screttas, J. Org. Chem., 1978, 43, 1064; (c) J. Barluenga, P. Bernad, and M. Yus, J. Chem. Soc., Chem. Commun., 1978, 847.

  32. (a) J. Barluenga, J. R. Fernandez, and M. Yus, J. Chem. Soc., Chem. Commun., 1985, 203; (b) J. Barluenga, J. L. Fernandez Simon, J. M. Concellon, and M. Yus, J. Chem. Soc., Perkin Trans. 1, 1988, 3339.

  33. (a) A. Guijarro and M. Yus, Tetrahedron Lett., 1993, 34, 2011; (b) F. F. Huerta, C. Gomez, A. Guijarro, and M. Yus, Tetrahedron, 1995, 51, 3375.

  34. G. R. Pettit, G. M. Cragg, M. I. Suffness, D. Gust, F. E. Boettner, M. Williams, J. A. Saenz-Renauld, P. Brown, and J. M. Schmidt, J. Org. Chem., 1984, 49, 4258.

    Google Scholar 

  35. (a) J. E. McCullough, M. T. Muller, A. J. Howells, A. Maxwell, J. O´Sullivan, R. S. Summerill, W. L. Parker, J. S. Wells, D. P. Bonner, and P. B. Fernandes, J. Antibiot., 1993, 46, 526; (b) M. Binaschi, G. Zagotto, M. Palumbo, F. Zunino, R. Farinosi, and G. Capranico, Cancer Res., 1997, 57, 1710.

  36. M. K. Ticku, T. P. Burch, and W. Davis, Adv. Biochem. Psychopharmacol., 1981, 29, 411.

    Google Scholar 

  37. F. Alonso, J. Melendez, and M. Yus, Helv. Chim. Acta, 2002, 85, 3262.

    Google Scholar 

  38. A. Guijarro, D. J. Ramon, and M. Yus, Tetrahedron, 1993, 49, 469.

    Google Scholar 

  39. (a) M. Yus, F. Foubelo, and J. V. Ferrandez, Chem. Lett., 2002, 726; (b) M. Yus, F. Foubelo, and J. V. Ferrandez, Tetrahedron, 2003, 59, 2083.

  40. N. G. Kundu, M. Pal, and B. Nandi, J. Chem. Soc., Perkin Trans. 1, 1998, 561 (and literature cited therein).

  41. J. Almena, F. Foubelo, and M. Yus, Tetrahedron, 1995, 51, 3351.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Sciences, Alicante University, 03080, Alicante, Spain

    F. Alonso, J. Meléndez & M. Yus

Authors
  1. F. Alonso
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. Meléndez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Yus
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Alonso, F., Meléndez, J. & Yus, M. Dilithiated synthons: synthesis of cyclic ethers. Russian Chemical Bulletin 52, 2628–2635 (2003). https://doi.org/10.1023/B:RUCB.0000019879.74515.27

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUCB.0000019879.74515.27

Search

Navigation