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Catalytic cycloalumination of 1,2-dienes in the total synthesis of natural grenadamide and lyngbyoic acid

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Abstract

An original method for the total synthesis of natural grenadamide and its precursor lyngbyoic acid with high stereoselectivity and yields was developed using the catalytic cycloalumination reaction of 1,2-dienes with Et3Al in the presence of 5 mol.% of Cp2ZrCl2 (Dzhemilev reaction) as a key step.

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References

  1. T. T. Talele, J. Med. Chem., 2016, 59, 8712.

    Article  CAS  Google Scholar 

  2. C. Lamberth, Tetrahedron, 2019, 75, 4365.

    Article  CAS  Google Scholar 

  3. N. Ye, H. Chen, E. A. Wold, P.-Y. Shi, J. Zhou, ACS Infect. Dis., 2016, 2, 382.

    Article  CAS  Google Scholar 

  4. M. Seki, K. Mori, Eur. J. Org. Chem., 2001, 20, 3797.

    Article  Google Scholar 

  5. N. Sitachitta; W. H. Gerwick, J. Nat. Prod., 1998, 61, 681.

    Article  CAS  Google Scholar 

  6. S. Jerhaoui, P. Poutree, J.-P. Djukic, J. Wencel-Delord, F. Colbert, Org. Chem. Front., 2018, 5, 409.

    Article  CAS  Google Scholar 

  7. T. Minuth, M. K. Boysen, Synthesis, 2010, 16, 2799.

    Google Scholar 

  8. H. Salim, O. Piva, Tetrahedron Lett., 2007, 48, 2059.

    Article  CAS  Google Scholar 

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

    Google Scholar 

  10. G. A. Abakumov, A. V. Piskunov, V. K. Cherkasov, I. L. Fedushkin, V. P. Ananikov, D. B. Eremin, E. G. Gordeev, I. P. Beletskaya, A. D. Averin, M. N. Bochkarev, A. A. Trifonov, U. M. Dzhemilev, V. A. D’yakonov, M. P. Egorov, A. N. Vereshchagin, M. A. Syroeshkin, V. V. Jouikov, A. M. Muzafarov, A. A. Anisimov, A. V. Arzumanyan, Yu. N. Kononevich, M. N. Temnikov, O. G. Sinyashin, Yu. H. Budnikova, A. R. Burilov, A. A. Karasik, V. F. Mironov, P. A. Storozhenko, G. I. Shcherbakova, B. A. Trofimov, S. V. Amosova, N. K. Gusarova, V. A. Potapov, V. B. Shur, V. V. Burlakov, V. S. Bogdanov, M. V. Andreev, Russ. Chem. Rev., 2018, 87, 393.

    Article  CAS  Google Scholar 

  11. U. M. Dzhemilev, V. A. D´yakonov, Top. Organomet. Chem., 2012, 41, 215.

    Article  Google Scholar 

  12. L. O. Khafizova, A. G. Ibragimov, G. N. Gil´fanova, L. M. Khalilov, U. M. Dzhemilev, Russ. Chem. Bull., 2001, 50, 2188.

    Article  CAS  Google Scholar 

  13. R. N. Kadikova, I. R. Ramazanov, T. P. Zosim, A. V. Yaroslavova, U. M. Dzhemilev, Tetrahedron, 2015, 71, 3290.

    Article  CAS  Google Scholar 

  14. J. C. Kwan, T. Meickle, D. Ladwa, M. Teplitski, V. Paul, H. Luesch, Mol. BioSyst., 2011, 7, 1205.

    Article  CAS  Google Scholar 

  15. W.-W. Sun, P. Cao, R.-Q. Mei, Y. Li, Y.-L. Ma, B. Wu, Org. Lett., 2014, 16, 480.

    Article  CAS  Google Scholar 

  16. J. Kuang, S. Ma, J. Org. Chem., 2009, 74, 1763.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    V. A. D´yakonov, A. A. Makarov, E. N. Andreev, E. Kh. Makarova, L. U. Dzhemileva, L. M. Khalilov & U. M. Dzhemilev

Authors
  1. V. A. D´yakonov
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  2. A. A. Makarov
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  3. E. N. Andreev
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  4. E. Kh. Makarova
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  5. L. U. Dzhemileva
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  6. L. M. Khalilov
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  7. U. M. Dzhemilev
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Corresponding author

Correspondence to V. A. D´yakonov.

Additional information

Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21—28, 2019, Moscow—Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0386–0389, February, 2020.

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D´yakonov, V.A., Makarov, A.A., Andreev, E.N. et al. Catalytic cycloalumination of 1,2-dienes in the total synthesis of natural grenadamide and lyngbyoic acid. Russ Chem Bull 69, 386–389 (2020). https://doi.org/10.1007/s11172-020-2772-0

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  • DOI: https://doi.org/10.1007/s11172-020-2772-0

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