Heck arylation of endocyclic enol ethers promoted by arenediazonium salts: methodology applications in natural substance synthesis with antitumor potential such as catechins, constituents of green tea, and flavonoid luteolin

• Grant number: 07/00350-0
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: October 01, 2007
• End date: February 18, 2009
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Fernanda Irene Bombonato
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

Bearing in mind; (1) the importance of the Heck arylations employing arenediazonium salts, (2) the great applicability of these reactions in the synthesis of pharmacologically active compounds, (3) as well as, our growing interest in the development of these arylating processes toward endocyclic enolethers: our main objectives on this research proposal are: (1) the development of the Heck arylation of endocyclic enolethers, and (2) the stereoselective total syntheses of natural products displaying antitumor activity. Such synthetic targets include the cathechins, and other structurally related compounds, such as the flavonoid luteoline.Two other associated objectives are: (a) to test the feasibility of employing boronic acids as surrogates for the arenediazonium salts in the Heck arylation (oxidative Heck), and (2) the potential application of chiral simulated moving bed chromatography (SMBC) as a mean to racemate resolution of compounds obtained through our Heck arylating processes. (AU)