Selective oxidation of lupeol by iodosylbenzene catalyzed by manganese porphyrins.
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2016
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Resumo
Manganese porphyrin-catalyzed oxidation of lupeol by iodosylbenzenewas achieved undermild conditionswith
low isolated yields but with remarkable selectivity, depending on the catalyst of choice. Mn(III) mesotetraphenylporphyrin
and Mn(III) meso-tetrakis(4-carbomethoxyphenyl)porphyrin provided an entry for the
preparation of 3β,30-dihydroxylup-20(29)-ene (6–14% yields), whereas Mn(III) β-octabromo-meso-tetrakis(4-
carbomethoxyphenyl)porphyrin led to 20-oxo-3β-hydroxy-29-norlupeol (6% yield), as single products.
Unreacted lupeol was recovered in quantitative yield. The oxidative transformations at lupeol C20 or C30 take
place with no need for protection of C3 hydroxyl moiety.
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Triterpene, Homogeneous catalyst
Citação
MARTINS, D. C. da S. et al. Selective oxidation of lupeol by iodosylbenzene catalyzed by manganese porphyrins. Catalysis Communications, v. 86, p. 104-107, 2016. Disponível em: <http://www.sciencedirect.com/science/article/pii/S1566736716302722>. Acesso em: 29 ago. 2017.