Synthesis of natural diterpenes through oxidation reactions of C-H bonds

• Grant number: 22/03331-7
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Effective date (Start): June 01, 2022
• Effective date (End): December 31, 2023
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Emílio Carlos de Lucca Júnior
• Grantee: Lucas Dias Pires Gonçalves
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant: 18/04837-6 - Oxidation of aliphatic C-H bonds catalyzed by transition metals, AP.JP

Abstract

The project aims to investigate a synthetic route to obtain two natural products: 2²,16±,17-trihydroxy-ent-cauran-19-oic acid, and wedelienone, through oxidations of C-H bonds. These products are found, respectively, in Mikania hirsutissima DC and Wedelia Chinensis plants and, as they belong to the kaurene class, we propose to synthesize them from kaurenoic acid. Both routes will be initiated by the syn dihydroxylation of kaurenoic acid. In order to synthesize the first one, it is expected to use Mn(CF3PDP) catalyst and an oxidizing agent to form alcohol at the C2 position. For wedelienone, the purpose is to perform oxidation at the C12 position from picolylimine-directed copper-catalyzed oxidation. (AU)