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<p>A method for modifying ring A of isoalantolactone to produce 4(<i>R</i>)-hydroxy-15-triazolyl derivatives was developed. The key steps in the transformation included sequential azidolysis of 13-methoxy-4,15-epoxy- 11,13-dihydroisoalantolactones and Cu-catalyzed azide-alkyne cycloaddition with various alkynes. A <i>retro</i>-Michael reaction of (11<i>R</i>)- and (11<i>S</i>)-stereoisomeric (4<i>R</i>)-hydroxy-13-methoxy-15-triazolyl-11,13- dihydroisoalantolactones using cesium carbonate in DMF formed isoalantolactone derivatives. The structures of three compounds were established by X-ray crystal structure analyses.</p>

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Synthesis and Cytotoxicity of 4-Hydroxy-15-Triazolyl-Substituted Isoalantolactone Derivatives

  • 期刊论文

  • 发表日期：

    2025年9月18日

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  • S. S. Patrushev,
  • T. V. Rybalova,
  • Yu. V. Meshkova,
  • M. K. Marenina,
  • T. G. Tolstikova,
  • E. E. Shults

摘要

A method for modifying ring A of isoalantolactone to produce 4(R)-hydroxy-15-triazolyl derivatives was developed. The key steps in the transformation included sequential azidolysis of 13-methoxy-4,15-epoxy- 11,13-dihydroisoalantolactones and Cu-catalyzed azide-alkyne cycloaddition with various alkynes. A retro-Michael reaction of (11R)- and (11S)-stereoisomeric (4R)-hydroxy-13-methoxy-15-triazolyl-11,13- dihydroisoalantolactones using cesium carbonate in DMF formed isoalantolactone derivatives. The structures of three compounds were established by X-ray crystal structure analyses.