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. 2022 Aug 5;87(15):10462-10466.
doi: 10.1021/acs.joc.2c01051. Epub 2022 Jul 21.

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

Victor C S Santana  1 , Eduardo C S Rocha  1 , Julian C S Pavan  2 , Vladimir C G Heleno  2 , Emilio C de Lucca Jr  1
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Selective Oxidations in the Synthesis of Complex Natural ent-Kauranes and ent-Beyeranes

Victor C S Santana et al. J Org Chem. .

Abstract

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.

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