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

Autor: Santana VCS; Institute of Chemistry, University of Campinas, 13083-970 Campinas, SP, Brazil., Rocha ECS; Institute of Chemistry, University of Campinas, 13083-970 Campinas, SP, Brazil., Pavan JCS; Research Center in Exact and Technological Sciences, University of Franca, 14404-600 Franca, SP, Brazil., Heleno VCG; Research Center in Exact and Technological Sciences, University of Franca, 14404-600 Franca, SP, Brazil., de Lucca EC Jr; Institute of Chemistry, University of Campinas, 13083-970 Campinas, SP, Brazil.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2022 Aug 05; Vol. 87 (15), pp. 10462-10466. Date of Electronic Publication: 2022 Jul 21.
DOI: 10.1021/acs.joc.2c01051
Abstrakt: 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(CF 3 -PDP) enabled the first application of a nondirected metal-catalyzed oxidation in an unactivated C-H bond in a total synthesis.
Databáze: MEDLINE
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