Skip to main content
SpringerLink
Log in

Metallacomplex catalysis in the synthesis of regular isoprenoids

  • Review
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

This brief review covers and systematizes the key results acquired using metal complex catalysts in both fundamental and applied research aimed at the development of methods and approaches for the production of practically important cyclic and linear isoprenoids, including vitamins, insect pheromones, and flavorants. Own works of the authors on the use of previously discovered novel reactions of homo- and cross-cyclomagnesiation of 1,2-dienes for the synthesis of compounds of isoprenoid structure are considered separately.

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

References

  1. A. J. Hadgen-Smit Jr., The Essential Oils, Vol. 1, Ed. E. Guentner, Van Nostrand Co., Inc., New York, 1948, p. 17.

  2. P. Bernfeld, Biogenesis of Natural Compounds, Pergamon Press, Oxford-London-New York-Paris, 1963, 1224 p.

    Google Scholar 

  3. P. B. Dzhevakov, M. A. Topchiy, A. A. Ageshina, L. I. Minaeva, S. A. Rzhevskiy, M. S. Nechaev, S. N. Osipov, A. F. Asachenko, Russ. Chem. Bull., 2020, 69, 2307; DOI: https://doi.org/10.1007/s11172-020-3038-6.

    Article  CAS  Google Scholar 

  4. V. A. Rozentsvet, D. M. Ulyanova, N. A. Sablina, M. G. Kuznetsova, P. M. Tolstoy, Russ. Chem. Bull., 2022, 71, 787; DOI: https://doi.org/10.1007/s11172-022-3479-1.

    Article  CAS  Google Scholar 

  5. R. D. Semba, Ann. Nutr. Metab., 2012, 61, 192; DOI: https://doi.org/10.1159/000343124.

    Article  CAS  PubMed  Google Scholar 

  6. E. F. Bell, Am. J. Clinic. Nutrition, 1987, 46, 183; DOI: https://doi.org/10.1093/ajcn/46.1.183.

    Article  CAS  Google Scholar 

  7. D. W. MacCorquadale, S. B. Binkley, S. A. Thayer, E. A. Doisy, J. Am. Chem. Soc., 1939, 61, 1928; DOI: https://doi.org/10.1021/ja01876a510.

    Article  Google Scholar 

  8. A. V. Semenovsky, W. A. Smit, V. F. Kucherov, Dokl. Akad. Nauk SSSR, 1965, 160, 1097.

    Google Scholar 

  9. W. A. Smit, A. V. Semenovsky, I. I. Brunovlenskaya, S. L. Portnova, V. F. Kucherov, Dokl. Akad. Nauk SSSR, 1965, 160, 849.

    CAS  Google Scholar 

  10. A. M. Moiseenkov, K. V. Lebedeva, B. A. Cheskis, Russ. Chem. Rev., 1984, 53, 989.

    Article  Google Scholar 

  11. M. E. Maurit, G. V. Smirnova, E. A. Parfenov, I. K. Sarycheva, N. A. Preobrazhenskii, Dokl. Akad. Nauk SSSR, 1961, 140, 1330.

    CAS  Google Scholar 

  12. O. Rollen, Angew. Chem., 1948, 60, 62; DOI: https://doi.org/10.1002/ange.19480600302.

    Google Scholar 

  13. G. Wilke, J. Polymer Sci., 1959, 38, 45; DOI: https://doi.org/10.1002/pol.1959.1203813305.

    Article  CAS  Google Scholar 

  14. G. Wilke, Angew. Chem., Int. Ed. 1963, 2, 105; DOI: https://doi.org/10.1002/anie.196301051.

    Article  Google Scholar 

  15. G. Wilke, E. W. Müller, Pat. Ger. 1140569, Chem. Abstr., 1963, 58, 11214g.

  16. A. Misono, Y. Uchida, M. Hidai, Y. Osawa, Bull. Chem. Soc. Jpn, 1966, 39, 2425; DOI: https://doi.org/10.1246/bcsj.39.2425.

    Article  CAS  Google Scholar 

  17. G. A. Tolstikov, U. M. Dzhemilev, in Sov. Sci., Chemistry Reviews, Vol. 17, Eds N. K. Kochetkov, M. E. Volpin, Soviet Scientific Reviews, Section B, GmbH: Harwood Chur, London-Paris-New York, 1985.

  18. G. A. Tolstikov, U. M. Dzhemilev, S. S. Shavanov, USSR Inventor’s Certificate 522165; Byul. izobret. [Inv. Bull.], 1976, 27 (in Russian).

  19. G. A. Tolstikov, U. M. Dzhemilev, G. Ye. Ivanov, USSR Inventor’s Certificate 493455; Byul. izobret. [Inv. Bull.], 1975, 44 (in Russian).

  20. G. A. Tolstikov, B. M. Mikhailov, V. A. Dorokhov, G. Yu. Gubaidullin, U. M. Dzhemilev; USSR Inventor’s Certificate 791717; Byul. izobret. [Inv. Bull.], 1980, 48 (in Russian).

  21. U. M. Dzhemilev, G. A. Tolstikov, R. I. Khusnutdinov, Metallokompleksnyy kataliz v khimii dienov [Metallacomplex Catalysis in Chemistry of Dienes], Nauka, Moscow, 2013, 748 p. (in Russian).

    Google Scholar 

  22. I. N. Nazarov, A. I. Kuznetsova, N. V. Kuznetsov, Russ. J. Gen. Chem., 1955, 25, 291.

    CAS  Google Scholar 

  23. A. D. Josey, J. Org. Chem., 1974, 39, 139; DOI: https://doi.org/10.1021/jo00916a004.

    Article  Google Scholar 

  24. D. Neibecker, M. Touma, I. Tkatchenko, Synthesis, 1984, 12, 1023; DOI: https://doi.org/10.1055/s-1984-31060.

    Article  Google Scholar 

  25. R. Jackstell, A. Grotevendt, D. Michalik, L. El Firdoussi, M. Beller, J. Organomet. Chem., 2007, 692, 4737; DOI: https://doi.org/10.1016/j.jorganchem.2007.06.039.

    Article  CAS  Google Scholar 

  26. W. Keim, M. Ruper, M. Schieren, J. Mol. Catal., 1983, 20, 139; DOI: https://doi.org/10.1016/0304-5102(83)83003-X.

    Article  CAS  Google Scholar 

  27. K. Takabe, T. Yamada, T. Katagiri, Synth. Commun., 1983, 13, 297; DOI: https://doi.org/10.1080/00397918308066979.

    Article  CAS  Google Scholar 

  28. US Pat. 3843742, Chem. Abstr., 1974, 69, 8738c.

  29. Pat. Jap. 50024922, Chem. Abstr., 1975, 70, 10347e.

  30. G. A. Tolstikov, U. M. Dzhemilev, S. S. Shavanov, S. R. Rafikov, Dokl. Akad. Nauk SSSR, 1975, 223, 354.

    CAS  Google Scholar 

  31. V. A. D’yakonov, Dzhemilev Reactions in Organic and Organometallic Synthesis, NOVA Sci. Publ., New York, 2010, 96 p.

    Google Scholar 

  32. U. M. Dzhemilev, A. G. Ibragimov, Russ. Chem. Bull., 1998, 47, 786; DOI: https://doi.org/10.1007/BF02498144.

    Article  CAS  Google Scholar 

  33. A. G. Ibragimov, L. O. Khafizova, G. N. Gil’fanova, U. M. Dzhemilev, Russ. Chem. Bull., 2002, 51, 2255; DOI: https://doi.org/10.1023/A:1022191520197.

    Article  CAS  Google Scholar 

  34. U. M. Dzhemilev, V. A. D’yakonov, L. O. Khafizova, A. G. Ibragimov, Tetrahedron, 2004, 60, 1287; DOI: https://doi.org/10.1016/j.tet.2003.10.063.

    Article  CAS  Google Scholar 

  35. V. A. D’yakonov, R. K. Timerkhanov, A. G. Ibragimov, U. M. Dzhemilev, Russ. Chem. Bull., 2007, 56, 2232; DOI: https://doi.org/10.1007/s11172-007-0349-9.

    Article  Google Scholar 

  36. V. A. D’yakonov, R. K. Timerkhanov, T. V. Tyumkina, U. M. Dzhemilev, Russ. Chem. Bull., 2009, 58, 2456; DOI: https://doi.org/10.1007/s11172-009-0344-4.

    Article  Google Scholar 

  37. V. A. D’yakonov, R. K. Timerkhanov, U. M. Dzhemilev, Russ. J. Org. Chem., 2010, 46, 807; DOI: https://doi.org/10.1134/S1070428010060060.

    Article  Google Scholar 

  38. V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, L. M. Khalilov, U. M. Dzhemilev, Russ. Chem. Bull., 2012, 61, 1943; DOI: https://doi.org/10.1007/s11172-012-0269-1.

    Article  Google Scholar 

  39. U. M. Dzhemilev, V. A. D’yakonov, Top. Organometal. Chem., 2012, 41, 215; DOI: https://doi.org/10.1007/3418_2012_38.

    Google Scholar 

  40. V. A. D’yakonov, R. A. Zinnurova, A. G. Ibragimov, U. M. Dzhemilev, Russ. J. Org. Chem., 2007, 43, 956; DOI: https://doi.org/10.1134/S1070428007070020.

    Article  Google Scholar 

  41. V. A. D’yakonov, A. A. Makarov, A. G. Ibragimov, L. M. Khalilov, U. M. Dzhemilev, Tetrahedron, 2008, 64, 10188; DOI: https://doi.org/10.1016/j.tet.2008.08.041.

    Article  Google Scholar 

  42. V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, L. M. Khalilov, U. M. Dzhemilev, Russ. J. Org. Chem., 2012, 48, 349; DOI: https://doi.org/10.1134/S1070428012030025.

    Article  Google Scholar 

  43. V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, U. M. Dzhemilev, Tetrahedron, 2013, 69, 8516; DOI: https://doi.org/10.1016/j.tet.2013.06.106.

    Article  Google Scholar 

  44. V. A. D’yakonov, A. A. Makarov, L. U. Dzhemileva, E. Kh. Makarova, E. K. Khusnutdinova, U. M. Dzhemilev, Chem. Commun., 2013, 49, 8401; DOI: https://doi.org/10.1039/C3CC44926B.

    Article  Google Scholar 

  45. V. A. D’yakonov, L. U. Dzhemileva, R. A. Tuktarova, A. A. Makarov, I. I. Islamov, A. R. Mulyukova, U. M. Dzhemilev, Steroids, 2015, 102, 110; DOI: https://doi.org/10.1016/j.steroids.2015.08.006.

    Article  PubMed  Google Scholar 

  46. V. A. D’yakonov, L. U. Dzhemileva, A. A. Makarov, A. R. Mulyukova, D. S. Baev, E. K. Khusnutdinova, T. G. Tolstikova, U. M. Dzhemilev, Bioorg. Med. Chem. Lett., 2015, 25, 2405; DOI: https://doi.org/10.1016/j.bmcl.2015.04.011.

    Article  PubMed  Google Scholar 

  47. V. A. D’yakonov, R. A. Tuktarova, L. U. Dzhemileva, S. R. Ishmukhametova, M. M. Yunusbaeva, U. M. Dzhemilev, Steroids, 2018, 138, 14; DOI: https://doi.org/10.1016/j.steroids.2018.06.002.

    Article  PubMed  Google Scholar 

  48. V. A. D’yakonov, R. A. Tuktarova, L. U. Dzhemileva, S. R. Ishmukhametova, M. M. Yunusbaeva, U. M. Dzhemilev, Steroids, 2018, 138, 6; DOI: https://doi.org/10.1016/j.steroids.2018.06.004.

    Article  PubMed  Google Scholar 

  49. L. U. Dzhemileva, V. A. D’yakonov, A. A. Makarov, E. N. Andreev, M. M. Yunusbaeva, U. M. Dzhemilev, Org. Biomol. Chem., 2017, 15, 470; DOI: https://doi.org/10.1039/C6OB02346K.

    Article  CAS  PubMed  Google Scholar 

  50. V. A. D’yakonov, A. A. Makarov, A. R. Salimova, E. N. Andreev, U. M. Dzhemilev, Mendeleev Commun., 2017, 27, 234; DOI: https://doi.org/10.1016/j.mencom.2017.05.005.

    Article  Google Scholar 

  51. V. A. D’yakonov, L. U. Dzhemileva, A. A. Makarov, E. N. Andreev, U. M. Dzhemilev, Russ. J. Org. Chem., 2016, 52, 1844; DOI: https://doi.org/10.1134/S107042801612023X.

    Article  Google Scholar 

  52. V. A. D’yakonov, A. A. Makarov, L. U. Dzhemileva, E. N. Andreev, U. M. Dzhemilev, Mendeleev Commun., 2017, 27, 122; DOI: https://doi.org/10.1016/j.mencom.2017.03.004.

    Article  Google Scholar 

  53. V. A. D’yakonov, A. A. Makarov, L. U. Dzhemileva, E. N. Andreev, U. M. Dzhemilev, ChemistrySelect, 2017, 2, 1211; DOI: https://doi.org/10.1002/slct.201601988.

    Article  Google Scholar 

  54. V. A. D’yakonov, I. I. Islamov, L. U. Dzhemileva, E. M. Khusainova, M. M. Yunusbaeva, U. M. Dzhemilev, Tetrahedron, 2018, 74, 4606; DOI: https://doi.org/10.1016/j.tet.2018.07.031.

    Article  Google Scholar 

  55. V. A. D’yakonov, I. I. Islamov, E. M. Khusainova, U. M. Dzhemilev, Mendeleev Commun., 2018, 28, 503; DOI: https://doi.org/10.1016/j.mencom.2018.09.017.

    Article  Google Scholar 

  56. V. A. D’yakonov, I. I. Islamov, A. A. Makarov, U. M. Dzhemilev, Tetrahedron Lett., 2017, 58, 1755; DOI: https://doi.org/10.1016/j.tetlet.2017.03.061.

    Article  Google Scholar 

  57. E. Negishi, T. Takahashi, Aldrich. Chim. Acta, 1985, 18, 31.

    CAS  Google Scholar 

  58. U. M. Dzhemilev, O. S. Vostrikova, G. A. Tolstikov, J. Organomet. Chem., 1986, 304, 17; DOI: https://doi.org/10.1016/S0022-328X(00)99674-8.

    Article  CAS  Google Scholar 

  59. W. R. Roush, A. P. Spada, Tetrahedron Lett., 1983, 24, 3693; DOI: https://doi.org/10.1016/S0040-4039(00)94511-8.

    Article  CAS  Google Scholar 

  60. S. Fung, J. B. Siddall, J. Am. Chem. Soc., 1980, 102, 6580; DOI: https://doi.org/10.1021/ja00541a045.

    Article  CAS  Google Scholar 

  61. W. R. Roush, T. A. Blizzard, J. Org. Chem., 1984, 49, 4332; DOI: https://doi.org/10.1021/jo00197a002.

    Article  CAS  Google Scholar 

  62. P. J. Kocienski, S. D. A. Street, C. Yeates, S. F. Cambell, J. Chem. Soc. Perkin Trans I, 1987, 2189; DOI: https://doi.org/10.1039/P19870002189.

  63. Pat. RU 2197465 C2 (2001); Byul. izobret.[Inv. Bull.], 27.01.2003, No. 3 (in Russian)

  64. Pat. RU 2186064 C2 (2001); Byul. izobret. [Inv. Bull.], 27.07.2002, No. 21 (in Russian)

  65. V. N. Odinokov, M. I. Mallyabaeva, A. Y. Spivak, G. A. Emel’yanova, U. M. Dzhemilev, Dokl. Chem., 2001, 380, 255; DOI: https://doi.org/10.1023/A:1011998504137.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    U. M. Dzhemilev, L. U. Dzhemileva & V. A. D’yakonov

Authors
  1. U. M. Dzhemilev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. U. Dzhemileva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. D’yakonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. D’yakonov.

Additional information

Vladimir Anatol’evich D’yakonov, born in 1980, Doctor of Chemical Sciences, Professor of the Russian Academy of Sciences, Leading Researcher at the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Candidate for Corresponding Membership of the Russian Academy of Sciences on the elections of 2022, specialist in the field of organic, organometallic, medicinal chemistry and catalysis, as well as the total synthesis of natural biologically active compounds and their derivatives. His works have made contributions to studies on the use of metallocarbocycles of non-transition metals in organic and organometallic synthesis, in the field of catalytic synthesis, and to studies of the properties of three-, five- and macrocyclic metallacycles based on non-transition metals (Mg, Al, Zn, In, B), as well as directed and selective catalytic functionalization of cluster compounds, assembling energy-rich polycyclic strained hydrocarbons based on norbornadienes, cycloheptatrienes, cyclooctatetraenes and cumulenes, and finally, one-pot methods for the synthesis of furans, phospholanes, including macrocyclic ionophores, and macrodiolides. He carried out research projects aimed at the synthesis of polycyclic hydrocarbons, which were successfully implemented during work on contracts with the Ministry of Defense of the Russian Federation for the development of fuels for volume-limited systems. He is the author of 132 articles, 5 books, and more than 120 patents for inventions; 10 Ph.D. theses were defended under his supervision. V. A. D’yakonov is a member of the editorial board of the Doklady Physical Chemistry Journal.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 2, pp. 404–414, February, 2023.

No human or animal subjects were used in this research.

The authors declare no competing interests.

The work on this review was financially supported by the Russian Science Foundation (Project No. 22-13-00160).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dzhemilev, U.M., Dzhemileva, L.U. & D’yakonov, V.A. Metallacomplex catalysis in the synthesis of regular isoprenoids. Russ Chem Bull 72, 404–414 (2023). https://doi.org/10.1007/s11172-023-3808-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3808-8

Key words

Search

Navigation