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Synthesis of a Macrocyclic Conjugate of the Diterpenoid Isosteviol and Glucuronic Acid

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Chemistry of Natural Compounds Aims and scope

A macrocyclic conjugate of the natural diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and glucuronic acid was synthesized for the first time. The conjugate contained two molecules of dihydroisosteviol β-D-glucuronoside joined by 1,8-octanedicarboxylate and 1,8-octanedicarbazoyl spacers.

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References

  1. O. V. Andreeva, R. R. Sharipova, I. Yu. Strobykina, and V. E. Kataev, Chem. Nat. Compd., 50, 465 (2014).

    Article  CAS  Google Scholar 

  2. R. R. Sharipova, B. F. Garifullin, O. V. Andreeva, I. Yu. Strobykina, O. B. Bazanova, and V. E. Kataev, Zh. Org. Khim., 51, 424 (2015).

    CAS  Google Scholar 

  3. B. F. Garifullin, O. V. Andreeva, I. Yu. Strobykina, V. M. Babaev, and V. E. Kataev, Macroheterocycles, 6, 184 (2013).

    Article  CAS  Google Scholar 

  4. O. V. Andreeva, I. Yu. Strobykina, O. N. Kataeva, O. B. Dobrynin, V. M. Babaev, I. Kh. Rizvanov, D. R. Islamov, and V. E. Kataev, Macroheterocycles, 6, 315 (2013).

    Article  CAS  Google Scholar 

  5. T.-C. Cheng, S. R. Roffler, S.-C. Tzou, K.-H. Chuang, Y.-C. Su, C.-H. Chuang, C.-H. Kao, C.-S. Chen, I.-H. Harn, K.-Y. Liu, T.-L. Cheng, and Y.-L. Leu, J. Am. Chem. Soc., 134, 3103 (2012).

    Article  CAS  PubMed  Google Scholar 

  6. S. A. K. Jongkees and S. G. Withers, J. Am. Chem. Soc., 133, 19334 (2011).

    Article  CAS  PubMed  Google Scholar 

  7. G. Hoever, L. Baltina, M. Michaelis, R. Kondratenko, L. Baltina, Jr., G. A. Tolstikov, H. W. Doerr, and J. Cinatl, Jr., J. Med. Chem., 48, 1256 (2005).

    Article  CAS  PubMed  Google Scholar 

  8. L. F. Tietze, H. J. Schuster, K. Schmuck, I. Schuberth, and F. Alves, Bioorg. Med. Chem., 16, 6312 (2008).

    Article  CAS  PubMed  Google Scholar 

  9. J. Becher, I. Seidel, W. Plass, and D. Klemm, Tetrahedron, 62, 5675 (2006).

    Article  CAS  Google Scholar 

  10. S. Andre, T. Velasco-Torrijos, R. Leyden, S. Gouin, M. Tosin, P. V. Murphy, and H.-J. Gabius, Org. Biomol. Chem., 7, 4715 (2009).

    Article  CAS  PubMed  Google Scholar 

  11. T. Velasco-Torrijos and P. V. Murphy, Tetrahedron: Asymmetry, 16, 261 (2005).

    Article  CAS  Google Scholar 

  12. G. N. Bollenback, J. W. Long, D. G. Benjamin, and J. A. Lindquist, J. Am. Chem. Soc., 77, 3310 (1955).

    Article  CAS  Google Scholar 

  13. V. E. Kataev, O. I. Militsina, I. Yu. Strobykina, G. I. Kovylyaeva, R. Z. Musin, O. V. Fedorova, G. L. Rusinov, M. N. Zueva, G. G. Mordovskoi, and A. G. Tolstikov, Khim.-farm. Zh., 40 (9), 12 (2006).

    Google Scholar 

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Acknowledgment

The work was sponsored by the Russian Science Foundation (Grant No. 14-50-00014).

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia, Ul. Arbuzova, 8

    O. V. Andreeva, R. R. Sharipova, B. F. Garifullin, I. Yu. Strobykina & V. E. Kataev

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  1. O. V. Andreeva
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  2. R. R. Sharipova
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  3. B. F. Garifullin
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  4. I. Yu. Strobykina
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  5. V. E. Kataev
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Corresponding author

Correspondence to V. E. Kataev.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2015, pp. 594–597.

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Andreeva, O.V., Sharipova, R.R., Garifullin, B.F. et al. Synthesis of a Macrocyclic Conjugate of the Diterpenoid Isosteviol and Glucuronic Acid. Chem Nat Compd 51, 689–692 (2015). https://doi.org/10.1007/s10600-015-1385-6

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  • DOI: https://doi.org/10.1007/s10600-015-1385-6

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