Total Synthesis of Argutanes

• Grant number: 11/23553-0
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Effective date (Start): May 01, 2012
• Effective date (End): February 28, 2013
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Luiz Fernando da Silva Júnior
• Grantee: Muhammad Nawaz
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

The total synthesis of argutanes A and B will be performed using as key step a ring contraction reaction promoted by hypervalent iodine. The route is highly convergent and requires the preparation of the east and west fragment from a common intermediate. The longest linear sequence will have only 10 steps. We are also planning to obtain boschniakine, boschniakinic acid, argutine A, and argutine B from a synthetic intermediate. The following biological activities tests will be formed: anti-tumor in the group of Prof. J. E. Carvalho, UNICAMP; b) malaria in the group of Prof. Alejandro Miguel Katzin, ICB-USP; c) Leishmaniasis in the group of Prof. Marcelo Dias Baruffi, FCFRP-USP.The functionalization of carbon-hydrogen bonds of alkanes has received a lot of attention in the last years. One of this C-H activation reaction is the benzylic oxidation. This transformation is normally performed with transition metals. However, it can also performed with the hypervalent iodine(V) reagent IBX. In the second part of this project we are planning to study the regioselectivity of the benzylic oxidation mediated by IBX. This results will help in the total synthesis of argutanes.