A,b-unsaturated diazoketones as hydroxylated piperidine alkaloids precursors

• Grant number: 14/03830-7
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: April 01, 2014
• End date: March 31, 2015
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Ketllyn Irene Zagato de Oliveira
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

This research project aims to study and expand the range of applications of unsaturated diazoketones. As bifunctional intermediates, these unsaturated compounds can be employed quickly and efficiently in the synthesis of several molecules of synthetic interest. Among them, are the class of alkaloids (indolizidine, quinolizidine, piperidine). Extensively studied by the scientific community, the hydroxylated alkaloids have interesting biological applications such as inhibition of glucosidases. For the synthesis of various hydroxylated piperidine alkaloids, as well as for the synthesis of its 2-substituted derivatives, a previous methodology recently studied by our research group will be applied. This method involves as the key transformations the Wolff rearrangement and a dihydroxylation reaction to furnish hydroxylated piperidine alkaloids in few steps.