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Synthesis and transformations of metallacycles. 45. Cross-cyclomagnesiation of 1,2-dienes in the synthesis of 5Z,9Z-dienoic acids, efficient inhibitors of human topoisomerase I

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Abstract

An original method for the synthesis of natural and synthetic 5Z,9Z-dienoic acids with high selectivity (>98%) and ~50% yields was elaborated. The method is based on a new Cp2TiCl2catalyzed cross-cyclomagnesiation reaction of terminal aliphatic and O-containing 1,2-dienes using Grignard reagents. The synthesized acids exhibited in vitro high inhibiting activity against human topoisomerase I.

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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, A. R. Mulyukova, R. A. Tuktarova, I. I. Islamov & U. M. Dzhemilev

  2. Bashkir State Medical University, 3 ul. Lenina, 450003, Ufa, Russian Federation

    L. U. Dzhemileva

Authors
  1. V. A. D’yakonov
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  2. L. U. Dzhemileva
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  3. A. A. Makarov
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  4. A. R. Mulyukova
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  5. R. A. Tuktarova
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  6. I. I. Islamov
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  7. U. M. Dzhemilev
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Corresponding author

Correspondence to V. A. D’yakonov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

For Part 44, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2135–2140, September, 2015.

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D’yakonov, V.A., Dzhemileva, L.U., Makarov, A.A. et al. Synthesis and transformations of metallacycles. 45. Cross-cyclomagnesiation of 1,2-dienes in the synthesis of 5Z,9Z-dienoic acids, efficient inhibitors of human topoisomerase I. Russ Chem Bull 64, 2135–2140 (2015). https://doi.org/10.1007/s11172-015-1128-7

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  • DOI: https://doi.org/10.1007/s11172-015-1128-7

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