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

Author(s)

Santana, Victor C. S. ; Rocha, Eduardo C. S. ; Pavan, Julian C. S. ; Heleno, Vladimir C. G. ; de Lucca Jr, Emilio C.

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. N/A, p. 5-pg., 2022-07-21.

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. (AU)

• FAPESP's process: 18/04837-6 - Oxidation of aliphatic C-H bonds catalyzed by transition metals
• Grantee: Emílio Carlos de Lucca Júnior
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 21/01918-8 - Late-stage C-H functionalization: using the position C19 of steviol as a directing group
• Grantee: Eduardo Crespi Souza Rocha
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• FAPESP's process: 19/27528-1 - The development of a catalytic system that avoids the oxidation of alcohols to the corresponding carbonyl compounds
• Grantee: Victor Camargo Stork Santana
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)