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Enantioselective Formal Synthesis of the Cytotoxic Topoisomerase II Inhibitor Deoxythysanone, Catalyzed by Chiral Spiroborate Ester

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Abstract

Bioactive pyranonaphthoquinone analogs, (1R,3S)-deoxythysanone, (1R,3S)-thysanone, and (1R,3S)-demethoxythysanone can be efficiently synthesized from a common intermediate product, (S)-3-methyl-3,4-dihydro-1H-isochromene-5,8-dione. We have developed a short synthetic route to pyranonaphthoquinone antibiotics, which involves enantioselective reduction of homobenzylic ketone in the presence of a chiral spiroborate catalyst with 87% enantiomeric excess as the key step. The subsequent oxa-Pectet–Spengler reaction, followed by oxidative demethylation, afforded deoxythysanone.

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ACKNOWLEDGMENTS

The authors are thankful to Department of Science and Technology and Department of Chemistry, University of Pune, for financial support and infrastructural facility; M. Chopade thanks the Ajintha Education Society for infrastructural facility.

Funding

This study was performed under financial support by the BCUD Dr. Babasaheb Ambedkar Marathwada University, Aurangabad.

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Authors and Affiliations

  1. Department of Chemistry, Sant Dnyaneshwar Mahavidyalaya, Soegaon, 431120, Aurangabad, India

    M. U. Chopade

  2. Department of Chemistry, Savitribai Phule University, 411007, Pune, India

    M. U. Chopade & M. D. Nikalje

  3. Department of Chemistry, Moreshwar College, 431114, Bhokardan, India

    H. S. Patil

  4. Dahiwadi College, 415508, Dahiwadi, India

    A. U. Chopade

Authors
  1. M. U. Chopade
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  2. M. D. Nikalje
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  3. H. S. Patil
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  4. A. U. Chopade
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Correspondence to M. U. Chopade.

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Chopade, M.U., Nikalje, M.D., Patil, H.S. et al. Enantioselective Formal Synthesis of the Cytotoxic Topoisomerase II Inhibitor Deoxythysanone, Catalyzed by Chiral Spiroborate Ester. Russ J Org Chem 56, 693–697 (2020). https://doi.org/10.1134/S1070428020040181

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