Study aiming to the convergent total synthesis of the aporphine alkaloid (R)-(-)-apomorphine

• Grant number: 14/09180-4
• Support Opportunities: Scholarships in Brazil - Master
• Effective date (Start): November 01, 2014
• Effective date (End): April 30, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Acordo de Cooperação: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal Investigator: Cristiano Raminelli
• Grantee: Ana Carolina de Avelar Muraca
• Host Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

Due to the considerable importance of 2-(trimethylsilyl)aryl triflates in the current context of the benzyne chemistry, we intend to develop the convergent total synthesis of the aporphine alkaloid (R)-(-)-apomorphine, which is used as medicine in the therapy of Parkinson's disease and in the treatment of erectile dysfunction, employing approach that presents in the key step [4+2] cycloaddition reaction followed by a [1,3] sigmatropic rearrangement of hydrogen between 1-methylene-1,2,3,4-tetrahydroisoquinoline and aryne, formed from its corresponding 2-(trimethylsilyl)aryl triflate, under relatively mild reaction conditions. (AU)