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Synthesis from (–)-α-Pinene of an Optically Active Macrocyclic Diesterdihydrazide with 2,6-Pyridinedicarboxylic and Adipic Acid Moities

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Chemistry of Natural Compounds Aims and scope

An optically active macrocyclic diesterdihydrazide with 2,6-pyridinedicarboxylic and adipic acid moieties was synthesized efficiently from available (–)-α-pinene through an intermediate hydroxyketone [1R-(1′-hydroxyethyl)-3R-(2″-hydroxyethyl)-2,2-dimethylcyclobutane) using successive [2 + 1]-reaction of the last with 2,6-pyridinedicarboxylic acid dichloride and [1 + 1]-condensation of the resulting diketodiester with adipic acid dihydrazide.

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References

  1. X. Y. Zhang and S. J. Li, Chem. Chem. Eng., 5, 1041 (2011).

    CAS  Google Scholar 

  2. M. Zh. Gao, J. H. Reibenspies, B. Wang, Z. L. Xu, and R. A. Zingaro, J. Heterocycl. Chem., 41, 899 (2004).

    Article  CAS  Google Scholar 

  3. G. Yu. Ishmuratov, G. R. Mingaleeva, R. R. Muslukhov, M. P. Yakovleva, O. O. Shakhanova, L. P. Botsman, and A. G. Tolstikov, Khim. Prir. Soedin., 195 (2011).

  4. R. V. Stevens, K. T. Chapman, C. A. Stubbs, W. W. Tam, and K. F. Albizati, Tetrahedron Lett., 23,4647 (1982).

    Article  CAS  Google Scholar 

  5. B. M. McKenzie, A. K. Miller, R. J. Wojtecki, J. C. Johnson, K. A. Burke, K. A. Tzeng, P. T. Mather, and S. J. Rowan, Tetrahedron, 64, 8488 (2008).

    Article  CAS  Google Scholar 

  6. G. Yu. Ishmuratov, M. P. Yakovleva, M. A. Shutova, N. R. Yaubasarov, R. R. Muslukhov, E. M. Vyrypaev, and A. G. Tolstikov, Macrogeterotsikly, 7, 321 (2014).

    CAS  Google Scholar 

  7. K. Weygand and G. Hilgetag, Organisch-chemische Experimentierkunst, Barth, Leipzig (1964).

    Google Scholar 

  8. T. Saton, T. Okuda, Y. Kaneko, and K. Yamakawa, Chem. Pharm. Bull., 32, 1401 (1984).

    Article  Google Scholar 

Download references

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Authors and Affiliations

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

    G. Yu. Ishmuratov, V. A. Vydrina, K. S. Denisova, M. P. Yakovleva, E. M. Vyrypaev & A. G. Tolstikov

  2. Birsk Branch of Bashkir State University, 10 Internatsional′naya St, Birsk, 452455, Russia

    R. R. Gazetdinov

Authors
  1. G. Yu. Ishmuratov
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  2. V. A. Vydrina
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  3. K. S. Denisova
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  4. M. P. Yakovleva
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  5. R. R. Gazetdinov
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  6. E. M. Vyrypaev
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  7. A. G. Tolstikov
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Corresponding author

Correspondence to G. Yu. Ishmuratov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2017, pp. 53–55.

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Ishmuratov, G.Y., Vydrina, V.A., Denisova, K.S. et al. Synthesis from (–)-α-Pinene of an Optically Active Macrocyclic Diesterdihydrazide with 2,6-Pyridinedicarboxylic and Adipic Acid Moities. Chem Nat Compd 53, 63–65 (2017). https://doi.org/10.1007/s10600-017-1912-8

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  • DOI: https://doi.org/10.1007/s10600-017-1912-8

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