4.5 Article

Solvent-Driven Selectivity on the One-Step Catalytic Synthesis of Manoyl Oxide Based on a Novel and Sustainable Zeolite Catalyst-Solvent System

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CATALYSIS LETTERS
卷 152, 期 5, 页码 1298-1307

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SPRINGER
DOI: 10.1007/s10562-021-03721-6

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Manoyl oxide; Solvent effects; Zeolites; Cyclization; Heterogeneous catalysis; Terpenoids; Green chemistry; Acid catalysis; Dehydration; Activation energy

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The study introduces a novel catalyst-solvent system that enables high-yield and large-scale production of the terpenoid manoyl oxide, with improved selectivity using a substrate-controlled methodology. The research also demonstrates the crucial role of solvents in catalysis, showing a decrease in activation energy barrier in the presence of appropriate solvents. Additionally, the acidity of the catalyst is identified as a key parameter for the process.
Application of a novel zeolite catalyst-solvent system for the sustainable one-step synthesis of the terpenoid manoyl oxide, the potential precursor of forskolin and ambrox. Manoyl oxide high-yield and large-scale production over a zeolite catalyst has been infeasible so far, while this system results in 90% yields at 135 degrees C and atmospheric pressure. Substrate-controlled methodology is used to achieve selectivity. Solvent-driven catalysis is shown, as the activation energy barrier decreases in the presence of appropriate solvents, being 62.7 and 93.46 kJmol(-1) for a glyme-type solvent and dodecane, respectively. Finally, catalyst acidity is key parameter for the process.

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