Mn aminopyridine oxidase mimics: Switching between biosynthetic-like and xenobiotic regioselectivity in C–H oxidation of (-)-ambroxide

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Abstract

The late-stage C–H oxofunctionalization of (-)-ambroxide with H2O2 in the presence of bioinspired honheme Mn complexes is reported. Adjusting the ligand architecture and absolute chirality, as well as tuning the reaction solvent, allows switching the catalysts’ selectivity between biosynthetic-like and bioorthogonal modes, thus directing the reaction towards either (+)-sclareolide or 2α-hydroxyambroxide, respectively. This opens the ways to 2,12-dihydroxyambroxide, 2α-hydroxysclareolide, ambroxide-2-one, ambroxide-2,12-dione, and several other, including previously unavailable, oxidized metabolites of (-)-ambroxide in synthetically meaningful yields, using the same catalyst systems.

Original languageEnglish
Pages (from-to)224-229
Number of pages6
JournalJournal of Catalysis
Volume399
DOIs
Publication statusPublished - Jul 2021

Keywords

  • Biomimetic chemistry
  • C–H activation
  • Late-stage functionalization
  • Natural products
  • Steroids

OECD FOS+WOS

  • 2.04 CHEMICAL ENGINEERING
  • 1.04 CHEMICAL SCIENCES
  • 1.04.EI CHEMISTRY, PHYSICAL
  • 2.04.II ENGINEERING, CHEMICAL

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