Manganese Porphyrin‐Catalyzed One‐Pot Oxidation of Lupeol: Efficient Conversion of Its Terminal Alkene Into Carboxylic Acids

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Abstract
The PhI(OAc) 2 ‐oxidation of the triterpene lupeol by manganese porphyrin was achieved, leading to 94% of lupeol conversion. Conditions aligned with principles of green chemistry, including the use of ethyl acetate as a solvent and iodobenzene diacetate as an oxidant, were studied. This approach led to the production of eight products from lupeol, notably achieving transformations at the C20 olefin moiety; six lupeol's products were isolated whereas the other two had their structures proposed supported on basic chemical tests (e.g., Fehling's test) and well‑established reactivity patterns in organic chemistry. These modifications were performed without the typical preceding protection of the C3 hydroxyl of lupeol, simplifying the synthetic route. Besides, the isopropenyl group of lupeol was converted to carboxylic acids through one‐pot oxidation. This study reinforces the promising use of manganese porphyrins as catalysts for the oxidative transformation of other natural products of biological interest.
Funding Information
  • Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
  • Fundação de Amparo à Pesquisa do Estado de Minas Gerais (APQ‐01200‐21)
  • Fundação de Amparo à Pesquisa do Estado de Minas Gerais (APQ‐00113‐24)
  • Conselho Nacional de Desenvolvimento Científico e Tecnológico (405824/2021‐1)
  • Conselho Nacional de Desenvolvimento Científico e Tecnológico (311504/2022‐1)

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