Studies toward stereoselective synthesis of alkaloid 275A

Author(s)

Jose Roberto Riston

• Document type: Master's Dissertation
• Press: Campinas, SP.
• Institution: Universidade Estadual de Campinas (UNICAMP). Instituto de Química
• Defense date: 2006-11-12

Examining board members

Ronaldo Aloise Pilli; Silvio do Desterro Cunha; Fernando Antonio Santos Coelho

• Advisor: Ronaldo Aloise Pilli

Abstract

This work consists in studies toward the stereoselective synthesis of alkaloid 275A (18, Figure 1). This alkaloid was isolated by Daly and co-workers from the skin of neotropical poison little frogs of Dendrobatidae family in 1986. His structure has an 1-azabicyclo[5.3.0]decane nucleus of great synthetic importance. To construct this nucleus we used, mainly, a-amidoalkylation reactions and ring close metathesis (RCM), starting with (S) proline (57, Scheme 1) (AU)