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<p>A series of terpene α-chlorohydrins was synthesized in 44–89% yields by the reduction of the corresponding α-chloro ketones using NaBH<sub>4</sub>. In turn, α-chloro ketones were synthesized from the secondary terpene alcohols by a one-pot procedure using the ClO<sub>2</sub>—DMF oxidative-chlorinating system. α-Chloro ketones demonstrated significantly higher antifungal activity than the corresponding chlorohydrins and oxygen-containing terpenoids and in some cases their activity is comparable to or exceed the activity of the antifungal reference drugs fluconazole and ketoconazole.</p>

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Chlorinated terpenoids of pinane structure: synthesis and antifungal activity

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • L. L. Frolova,
  • A. V. Popov,
  • D. V. Sudarikov,
  • E. U. Ipatova,
  • L. E. Nikitina,
  • S. A. Lisovskaya,
  • A. V. Kutchin

摘要

A series of terpene α-chlorohydrins was synthesized in 44–89% yields by the reduction of the corresponding α-chloro ketones using NaBH4. In turn, α-chloro ketones were synthesized from the secondary terpene alcohols by a one-pot procedure using the ClO2—DMF oxidative-chlorinating system. α-Chloro ketones demonstrated significantly higher antifungal activity than the corresponding chlorohydrins and oxygen-containing terpenoids and in some cases their activity is comparable to or exceed the activity of the antifungal reference drugs fluconazole and ketoconazole.