Synthesis of substituted 7-azanorbornanes by intramolecular mannich reaction: application to asymmetric synthesis of epibatidine

• Grant number: 13/18700-9
• Support Opportunities: Scholarships in Brazil - Master
• Start date: January 01, 2014
• End date: January 31, 2015
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Alvaro Takeo Omori
• Grantee: Ronaldo Epifanio de Oliveira Filho
• Host Institution: Centro de Ciências Naturais e Humanas (CCNH). Universidade Federal do ABC (UFABC). Ministério da Educação (Brasil). Santo André , SP, Brazil
• Associated research grant: 09/00617-2 - Biocatalysis: the use of plant cells and lipases in organic synthesis - application on asymmetric synthesis of biologically active compounds, AP.JP

Abstract

This proposal aims the synthesis and reactivity studies of substituted 7-azanorbornanes. Since this class of compounds is well investigated, mainly by the discovery of (-)-Epibatidine, the main objective is investigate the intramolecular Mannich reaction (developed by Rapoport and coworkers) with less complex substrates. Although the 5-endo-trig cyclization is unfavored according to Baldwin rules, the high reactivity of iminium ions make the cyclization favored. Starting materials include pyroglutamic acid, ethyl acrylate and nitromethane (low costs reagents). Depending on success in obtaining the bicyclic compounds we can apply this methodology to synthesize Epibatidine. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

DE OLIVEIRA FILHO, RONALDO E.; OMORI, ALVARO T.. Recent Syntheses of Frog Alkaloid Epibatidine. Journal of the Brazilian Chemical Society, v. 26, n. 5, p. 837-850, MAY 2015. (09/00617-2, 13/18700-9)