Selective Oxidations in the Synthesis of Complex Natural ent-Kauranes and ent-Beyeranes.

Syntheses of two natural products derived from the ent-kaurene kaurenoic acid are described for the first time using regio- and diastereoselective oxidations. Palladium- and manganese-mediated oxidations were used to accomplish the syntheses of two ent-beyerane metabolites. The use of the White-Gormisky-Zhao catalyst Mn(CF3-PDP) enabled the first application of a nondirected metal-catalyzed oxidation in an unactivated C-H bond in a total synthesis.

Citation

Victor C S Santana, Eduardo C S Rocha, Julian C S Pavan, Vladimir C G Heleno, Emilio C de Lucca. Selective Oxidations in the Synthesis of Complex Natural ent-Kauranes and ent-Beyeranes. The Journal of organic chemistry. 2022 Aug 05;87(15):10462-10466

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PMID: 35862248

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