Skip to main content
SpringerLink
Log in

Hydroboration–Oxidation of Terpenoids in Targeted Syntheses of Low-Molecular-Mass Bioregulators

  • Published:
Chemistry of Natural Compounds Aims and scope

Examples of hydroboration–oxidation of natural mono-, sesqui-, di-, and triterpenoids are reviewed. Diborane, BH3·THF, BH3·Me2S, disiamylborane, thexylborane, dicyclohexylborane, 9-borabicyclo[3,3,1]nonane (9-BBN), and diisopinocampheylborane are used as the hydroboration reagents; H2O2 mixed with KOH, NaOH, and NaOAc, as the oxidants. Most of the examples address mono- and sesquiterpenoids with far fewer describing di- and triterpenoids.

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. B. M. Mikhailov and Yu. N. Bubnov, Organoboron Compounds in Organic Synthesis [in Russian], Nauka, Moscow, 1977, 516 pp.

    Google Scholar 

  2. H. C. Brown and S. Krishnamurthy, Tetrahedron, 35, 567 (1979).

    CAS  Google Scholar 

  3. H. C. Brown and P. V. Ramachandran, Reduction in Organic Synthesis. Recent Advances and Practical Application, ACS Symposium Series 641, 1996.

  4. V. V. Plemenkov, Introduction to the Chemistry of Natural Products [in Russian], Kazan, 2001, 376 pp.

  5. H. C. Brown, K. P. Singh, and B. J. Garner, J. Organomet. Chem., 1, No. 1, 2 (1963).

    CAS  Google Scholar 

  6. Tryptophan Medicinal Chemistry. Chemical Encyclopedia in 5 Volumes [in Russian], Bol′shaya Rossiiskaya Entsiklopediya, Moscow, 1998, Vol. 5, 784 pp.

  7. M. Julia and P. Roy, Tetrahedron, 42, 5003 (1986).

    CAS  Google Scholar 

  8. J. Wolinsky and R. H. Bedoukian, J. Org. Chem., 41, 278 (1976).

    CAS  Google Scholar 

  9. A. F. Thomas and Y. Bessiere, Nat. Prod. Rep., 291 (1989).

    CAS  Google Scholar 

  10. L. A. Kheifits and V. M. Dashunin, Fragrances and Other Products for Perfumery [in Russian], Khimiya, Moscow, 1994, 256 pp.

    Google Scholar 

  11. P. I. Fedorov, T. P. Fedorova, V. P. Sheverdov, G. P. Pavlov, and A. V. Eremkin, Russ. J. Org. Chem., 52, 806 (2016).

    CAS  Google Scholar 

  12. J. C. Chalchat, R. P. Garry, A. Michet, and E. Lecomte, Flavour Fragrance J., 7, 107 (1992).

    CAS  Google Scholar 

  13. G. Ohloff and G. Uhde, Helv. Chim. Acta, 48, 10 (1965).

    CAS  Google Scholar 

  14. H. C. Brown and C. D. Pfaffenberger, Tetrahedron, 31, 925 (1975).

    CAS  Google Scholar 

  15. J. de P. Teresa, A. F. Mateos, and R. R. Ganzalez, Tetrahedron Lett., 23, 3405 (1982).

  16. T. Money and M. K. C. Wong, Stud. Nat. Prod. Chem., 16, 123 (1995).

    CAS  Google Scholar 

  17. H. C. Brown and K. Murray, J. Amer. Chem. Soc., 81, 4108 (1959).

    CAS  Google Scholar 

  18. H. C. Brown and K. Murray, J. Org. Chem., 26, 631 (1961).

    CAS  Google Scholar 

  19. T. Sakai, K. Nakajima, K. Yoshihara, and T. Sakan, Tetrahedron, 36, 3115 (1980).

    CAS  Google Scholar 

  20. D. R. Williams and J. G. Phillips, J. Org. Chem., 46, 5452 (1981).

    CAS  Google Scholar 

  21. I. Blank, W. Grosch, W. Eisenreich, A. Bacher, and J. Firl, Helv. Chim. Acta, 73, 1250 (1990).

    CAS  Google Scholar 

  22. S. P. Chavan, R. K. Kharul, A. K. Sharma, and S. P. Chavan, Tetrahedron: Asymmetry, 12, 2985 (2001).

    CAS  Google Scholar 

  23. G. Yu. Ishmuratov, M. P. Yakovleva, V. A. Vydrina, and G. A. Tolstikov, Khim. Rastit. Syr′ya, 5 (2008).

  24. G. Yu. Ishmuratov, E. R. Latypova, V. S. Tukhvatshin, A. A. Smol′nikov, R. R. Muslukhov, N. M. Ishmuratova, and R. F. Talipov, Chem. Nat. Compd., 48, 978 (2013).

  25. S. A. Voitkevich, 865 Fragrances for Perfumery and Household Chemistry [in Russian], Pishchevaya Promyshlennost′, Moscow, 1994, 594 pp.

  26. K. H. Schulte-Elte and G. Ohloff, Helv. Chim. Acta, 50, 153 (1967).

    CAS  Google Scholar 

  27. J. A. Moreira and A. G. Correa, Tetrahedron: Asymmetry, 14, 3787 (2003).

    CAS  Google Scholar 

  28. J. M. H. Lu, M. V. Perkins, and H. J. Griesser, Tetrahedron, 69, 6468 (2013).

    CAS  Google Scholar 

  29. H. Sasaki, H. Taguchi, T. Endo, I. Yosioka, and Y. Iitaka, Chem. Pharm. Bull., 29, 1636 (1981).

    CAS  Google Scholar 

  30. G. Schmid and W. Hofheinz, J. Am. Chem. Soc., 105, 624 (1983).

    CAS  Google Scholar 

  31. N. Balu, J. V. Thomas, and S. V. Bhat, J. Med. Chem., 34, 2821 (1991).

    CAS  PubMed  Google Scholar 

  32. X.-X. Xu, J. Zhu, D.-Z. Huang, and W.-S. Zhou, Acta Chim. Sin., 42, 940 (1984).

    CAS  Google Scholar 

  33. F. Korner, M. Schurmann, H. Preut, and W. Kreiser, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 56, 74 (2000).

  34. Z. G. Brill, M. L. Condakes, C. P. Ting, and T. J. Maimone, Chem. Rev., 117, 11753 (2017).

    CAS  PubMed  PubMed Central  Google Scholar 

  35. T. Ando and R. Yamakawa, Nat. Prod. Rep., 32, 1007 (2015).

    CAS  PubMed  Google Scholar 

  36. J. Casanovas, A. M. Namba, S. Leon, G. L. B. Aquino, G. V. J. da Silva, and C. Aleman, J. Org. Chem., 66, 3775 (2001).

    CAS  PubMed  Google Scholar 

  37. M. Nasuda, M. Ohmori, K. Ohyama, and Y. Fujimoto, Chem. Pharm. Bull., 60, 681 (2012).

    CAS  PubMed  Google Scholar 

  38. V. Khanna and P. H. Ladwa, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 26, 816 (1987).

  39. Yu. S. Demidova, E. V. Suslov, O. A. Simakova, K. P. Volcho, N. F. Salakhutdinov, I. L. Simakova, and D. Yu Murzin, J. Mol. Catal. A: Chem., 420, 142 (2016).

    CAS  Google Scholar 

  40. D. C. Harrowven, D. D. Pascoe, D. Demurtas, and H. O. Bourne, Angew. Chem., Int. Ed., 44, 1221 (2005).

  41. S. Serra and I. Nobile, Tetrahedron: Asymmetry, 22, 1455 (2011).

    CAS  Google Scholar 

  42. K. P. Volcho, L. N. Rogoza, N. F. Salakhutdinov, A. G. Tolstikov, and G. A. Tolstikov, Preparative Chemistry of Terpenoids. Part 1. Bicyclic Monoterpenoids [in Russian], Izd. SO RAN, Novosibirsk, 2005, 265 pp.

  43. S. P. Acharya, H. C. Brown, A. Suzuki, S. Nozawa, and M. Itoh, J. Org. Chem., 34, 3015 (1969).

    CAS  Google Scholar 

  44. J. Beckmann, D. Dakternieks, A. Duthie, S. L. Floate, R. C. Foitzik, and C. H. Schiesser, J. Organomet. Chem., 689, 909 (2004).

    CAS  Google Scholar 

  45. J. Lhomme and G. Ourisson, Tetrahedron, 24, 3201 (1968).

    CAS  Google Scholar 

  46. S. Berkman, J. C. Morrell, and G. Egloff, Catalysis: Inorganic and Organic, Reinhold Publ. Co., New York, 1940 [Russian translation by G. M. Tsiguro, Moscow, Leningrad, 1949, 743 pp]; W. F. Erman, J. Am. Chem. Soc., 86, 2887 (1964).

  47. F. Bondavalli, P. Schenone, and A. Ranise, Synthesis, 830 (1979).

    Google Scholar 

  48. F. Bondavalli, P. Schenone, A. Ranise, and S. Lanteri, J. Chem. Soc., Perkin Trans. 1, 2626 (1980).

  49. H. C. Brown and A. Suzuki, J. Am. Chem. Soc., 89, 1933 (1967).

    CAS  Google Scholar 

  50. S. P. Acharya and H. C. Brown, J. Am. Chem. Soc., 89, 1925 (1967).

    CAS  Google Scholar 

  51. W. Cocker, P. V. R. Shannon, and P. A. Staniland, J. Chem. Soc. C, 489 (1967).

  52. F. Z. Macaev and A. V. Malkov, Tetrahedron, 62, 9 (2006).

    CAS  Google Scholar 

  53. G. Zweifel and H. C. Brown, J. Am. Chem. Soc., 86, 393 (1964).

    CAS  Google Scholar 

  54. J. S. Cha, Bull. Korean Chem. Soc., 30, 1658 (2009).

    CAS  Google Scholar 

  55. R. Croteau, D. M. Satterwhite, D. E. Cane, and C. C. Chang, J. Biol. Chem., 263, 10063 (1988).

    CAS  PubMed  Google Scholar 

  56. U. P. Dhokte and H. C. Brown, J. Org. Chem., 62, 865 (1997).

    CAS  Google Scholar 

  57. H. C. Brown and G. Zweipel, J. Am. Chem. Soc., 83, 2544 (1961).

    CAS  Google Scholar 

  58. H. C. Brown and G. Zweipel, J. Am. Chem. Soc., 89, 561 (1967).

    CAS  Google Scholar 

  59. J. Beckmann, D. Dakternieks, A. Duthie, S. L. Floate, R. C. Foitzik, and C. H. Schiesser, J. Organomet. Chem., 689, 909 (2004).

    CAS  Google Scholar 

  60. J. C. Braun and G. S. Fisher, Tetrahedron Lett., 9 (1960).

  61. L. L. Frolova, Candidate Dissertation, Inst. Org. Chem., USC RAS, Ufa, 2005, 143 pp.

    Google Scholar 

  62. S.-l. Liao, S.-b. Shang, H.-y. Si, M.-g. Shen, X.-p. Rao, and Z.-q. Song, Chem. Ind. For. Prod., 33 (2015).

  63. Y. Chretien-Bessiere, Bull. Soc. Chim. Fr., 2182 (1964).

  64. Y. Chretien-Bessiere and G. Boussac, Bull. Soc. Chim. Fr., 4728 (1967).

  65. J. Scianowski, Z. Rafinski, A. Szuniewicz, and A. Wojtczak, Tetrahedron, 65, 10162 (2009).

    CAS  Google Scholar 

  66. O. A. Banina, D. V. Sudarikov, Yu. V. Krymskaya, L. L. Frolova, and A. V. Kuchin, Chem. Nat. Compd., 51, 261 (2015).

    CAS  Google Scholar 

  67. Y. Bessiere-Chretien and B. Meklat, Bull. Soc. Chim. Fr., 2591 (1971).

  68. P. F. Vlad, N D. Ungur, and V. B. Perutskii, SU Pat. 1,498,767, Aug. 7, 1989; Byull. Izobret., No. 29 (1989).

  69. D. S. Dodd and A. C. Oehlschlage, J. Org. Chem., 57, 2794 (1992).

    CAS  Google Scholar 

  70. K. Ishihara, H. Ishibashi, and H. Yamamoto, J. Am. Chem. Soc., 124, 3647 (2002).

    CAS  PubMed  Google Scholar 

  71. P. Weyerstahl, H. Marschall, U. Splittgerber, and D. Wolf, Liebigs Ann. Chem., 1997, 1783 (1997).

    Google Scholar 

  72. M. Gonzalez-Sierra, M. de los A. Laborde, and E.A. Ruveda, Synth. Commun., 17, 431 (1987).

  73. M. V. Kadival, M. S. R. Nair, and S. C. Bhattacharyya, Tetrahedron, 23, 1241 (1967).

    CAS  Google Scholar 

  74. A. Matsuo, H. Nozaki, T. Maeda, M. Nakayama, Y. Kushi, and S. Hayashi, J. Chem. Soc., Chem. Commun., 568 (1977).

  75. R. Shankaranarayan, S. C. Bisarya, and S. Dev, Tetrahedron, 33, 1207 (1976).

    Google Scholar 

  76. V. V. Ramana Rao and D. Devaprabhakara, Tetrahedron, 34, 223 (1978).

    Google Scholar 

  77. F. Y. Edamura and A. Nickon, J. Org. Chem., 35, 1509 (1970).

    CAS  Google Scholar 

  78. E. Dimitriadis and R. A. Massy-Westropp, Aust. J. Chem., 35, 1895 (1982).

    CAS  Google Scholar 

  79. E. Dimitriadis and R. A. Massy-Westropp, Phytochemistry, 23, 1325 (1984).

    CAS  Google Scholar 

  80. S. Carboni, A. Da Settimo, V. Malaguzzi, A. Marsili, and P. L. Pacini, Tetrahedron Lett., 3017 (1965).

  81. G. Buchi, F. Greuter, and T. Tokoroyama, Tetrahedron Lett., 827 (1962).

  82. S. P. Acharya and H. C. Brown, J. Org. Chem., 35, 3874 (1970).

    CAS  Google Scholar 

  83. A. R. Hochstetler, J. Org. Chem., 37, 1883 (1972).

    CAS  Google Scholar 

  84. M. M. Mehra, K. G. Deshpande, B. B. Ghatge, and S. C. Bhattacharyya, Tetrahedron, 23, 2469 (1967).

    CAS  Google Scholar 

  85. R. Naf, A. Velluz, W. Thommen, R. Brauchli, C. Sigwart, and J.-M. Gaudin, Flavour Fragrance J., 8, 307 (1993).

    Google Scholar 

  86. M. Kobayashi, B. W. Son, Y. Kyogoku, and I. Kitagawa, Chem. Pharm. Bull., 32, 1667 (1984).

    CAS  Google Scholar 

  87. P. Pesnelle and G. Ourisson, J. Org. Chem., 30, 1744 (1965).

    CAS  Google Scholar 

  88. G. Buchi, W. D. MacLeod, and J. Padilla, J. Am. Chem. Soc., 86, 4438 (1964).

    Google Scholar 

  89. A. Mehdinia, N. S. Fumani, and H. Rezaei, J. Persian Gulf, 5, 51 (2014).

    Google Scholar 

  90. C. M. Beechan, C. Djerassi, J. S. Finer, and J. Clardy, Tetrahedron Lett., 2395 (1977).

  91. S. P. Acharya and H. C. Brown, J. Org. Chem., 35, 196 (1970).

    CAS  Google Scholar 

  92. P. Brun and P. Waegell, Tetrahedron, 32, 1137 (1976).

    CAS  Google Scholar 

  93. P. Rani Bai, S. Y. Kamat, B. B. Ghatge, K. K. Chakravarti, and S. C. Battacharyya, Tetrahedron, 21, 629 (1965).

    Google Scholar 

  94. J. Lhomme and G. Ourisson, Tetrahedron, 24, 3167 (1968).

    CAS  Google Scholar 

  95. S. F. Arantes, J. R. Hanson, and P. B. Hitchcock, J. Chem. Res., Synop., 531 (2003).

  96. N. H. Anderson, Y. Ohta, A. Moore, and C.-L. W. Tseng, Tetrahedron, 34, 41 (1978).

    Google Scholar 

  97. B. E. Cross and P. L. Myers, J. Chem. Soc. C, 471 (1968).

  98. A. W. Burgstahler and J. N. Marx, Tetrahedron Lett., 3333 (1964).

  99. J. W. Huffman, T. Kamiya, L. H. Wright, J. J. Schmid, and W. Herz, J. Org. Chem., 31, 4128 (1966).

    CAS  Google Scholar 

  100. J. W. Huffman, J. A. Alford, and R. R. Sobti, J. Org. Chem., 35, 473 (1970).

    CAS  Google Scholar 

  101. J. C. W. Chien, J. Am. Chem. Soc., 82, 4762 (1960).

    CAS  Google Scholar 

  102. D. K. Black and G. W. Hedrick, J. Org. Chem., 32, 3758 (1967).

    CAS  Google Scholar 

  103. V. A. Vydrina, A. A. Kravchenko, M. P. Yakovleva, R. R. Muslukhov, A. G. Tolstikov, and G. Yu. Ishmuratov, Chem. Nat. Compd., 54, 478 (2018).

    CAS  Google Scholar 

  104. J. C. Sircar and G. S. Fisher, J. Org. Chem., 34, 404 (1969).

    CAS  Google Scholar 

  105. J. W. ApSimon, P. V. Demarco, and J. Lemke, Can. J. Chem., 43, 2793 (1965).

    CAS  Google Scholar 

  106. R. E. Ireland and L. N. Mander, J. Org. Chem., 34, 142 (1969).

    CAS  Google Scholar 

  107. R. Batista, P. A. Garcia, M. A. Castro, J. M. M. del Corral, N. L. Speziali, F. de P. Varotti, R. C. de Paula, L. F. Garcia-Fernandes, A. Francesch, A. S. Feliciano, and A. B. de Oliveira, Eur. J. Med. Chem., 62, 168 (2013).

  108. H. C. Vieira, J. A. Takahashi, and M. A. D. Boaventura, J. Agric. Food Chem., 50, 3704 (2002).

    CAS  PubMed  Google Scholar 

  109. R. R. Sobti and S. Dev, Tetrahedron Lett., 33, 3939 (1966).

    Google Scholar 

  110. Y. Kitahara and A. Yoshikoshi, Tetrahedron Lett., 1771 (1964).

  111. J. R. Hanson, P. B. Hitchcock, A. G. Jarvis, A. H. Ratcliffe, and E. M. Rodriguez-Perez, J. Chem. Soc., Perkin Trans. 1, 41 (1992).

  112. W. Dalziel, B. Hesp, K. M. Stevenson, and J. A. J. Jarvis, J. Chem. Soc., Perkin Trans. 1, 2841 (1973).

  113. L. G. Matyukhina, Zh. Obshch. Khim., 46, 2759 (1976).

    CAS  Google Scholar 

  114. L. G. Matyukhina and I. A. Saltykova, SU Pat. 505,621, Mar. 5, 1976; Byull. Izobret., No. 9 (1976).

  115. G. A. Tolstikov, O. B. Flekhter, E. E. Shul′ts, L. A. Baltina, and A. G. Tolstikov, Khim. Interesakh Ustoich. Razvit., 1 (2005).

  116. M. Dracinsky, S. Hybelbauerova, J. Sejbal, and M. Budesinsky, Collect. Czech. Chem. Commun., 71, 1131 (2006).

    CAS  Google Scholar 

  117. E. Klinotova, S. Bosak, and A. Vystrcil, Collect. Czech. Chem. Commun., 43, 2204 (1978).

    CAS  Google Scholar 

  118. Y. Inubushi, T. Sano, and Y. Tsuda, Tetrahedron Lett., 1303 (1964).

Download references

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    M. P. Yakovleva, V. A. Vydrina, A. A. Kravchenko & G. Yu. Ishmuratov

Authors
  1. M. P. Yakovleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Vydrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. Yu. Ishmuratov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. P. Yakovleva.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yakovleva, M.P., Vydrina, V.A., Kravchenko, A.A. et al. Hydroboration–Oxidation of Terpenoids in Targeted Syntheses of Low-Molecular-Mass Bioregulators. Chem Nat Compd 56, 1–26 (2020). https://doi.org/10.1007/s10600-020-02935-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-020-02935-1

Keywords

Search

Navigation