Total synthesis and evaluation of the cytotoxic activity of cacofurans A and B

• Grant number: 17/19953-9
• Support type: Scholarships in Brazil - Scientific Initiation
• Effective date (Start): November 01, 2017
• Effective date (End): October 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry
• Principal Investigator: Júlio Cezar Pastre
• Grantee: Pedro Manoel Barreto de Abreu
• Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant: 14/26378-2 - Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity, AP.JP

Abstract

Cacofurans A and B are diterpenes with a labdane skeleton found in marine species of Cacospongia sp., marine sponges which present the production of toxic substances as one of their defense mechanisms. This characteristic allows that those substances may be prototypes for the development of new therapeutic agents for the treatment of diseases, such as cancer, by triggering cell death. This project aims the total synthesis of cacofurans A and B, and the evaluation of the cytotoxic activity against cancer cell lines. In the proposed synthetic route, Suárez photochemical reaction is employed as the key step, a radicalar transformation which forges the tetrahydrofuran ring, that is present in these natural products. A selective addition of an organometallic to a carbonyl compound is proposed in this work, in order to achieve the stereogenic carbinolic center, which is present on the side chain of cacofurans A and B. (AU)