The use of a,b-unsaturated diazoketones with Z geometry in the direct construction of functionalized indolizidine skeletons: application in the synthesis of dehydrodemethylpumiliotoxins

• Grant number: 13/26399-7
• Support Opportunities: Scholarships in Brazil - Master
• Start date: April 01, 2014
• End date: July 31, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Meire Yasuko Kawamura
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated scholarship(s): 15/11793-7 - Synthesis of Inimosugars with Piperidine Core from a,b-Unsaturated Diazoketones with Z Geometry, BE.EP.MS

Abstract

Pumiliotoxins and their congeners are a class of compounds isolated from the skin of some frogs from the Dendrobatidae, Mantellidae, Bufonidae, e Myobatrachidae families, possessing interesting pharmacologic activities (cardiotonic activity in low concentrations). Because of the big number of compounds among these toxins (about 100), synthetic methodologies that provide the preparation of these compounds (as well as analogues) in great amounts and in a fast and efficient way using common intermediates, are very important for application in chemical-biology. This project aims the synthesis of these compounds, more specific of the dehydrodemethylpumiliotoxins, from a,b-unsatutated diazoketones with Z geometry. (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)

KAWAMURA, MEIRE Y.; TALERO, ALEXANDER G.; SANTIAGO, JOAO V.; GARAMBEL-VILCA, EDSON; ROSSET, ISAC G.; BURTOLOSO, ANTONIO C. B.. Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-L-serinal. Journal of Organic Chemistry, v. 81, n. 21, p. 10569-10575, NOV 4 2016. (13/18009-4, 13/26399-7, 13/25504-1)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

KAWAMURA, Meire Yasuko. The use of α,β-Unsaturated Diazoketones with Z Geometry in the Direct Construction of Functionalized Indolizidine and Piperidine Skeletons. 2016. Master's Dissertation - Universidade de São Paulo (USP). Instituto de Química de São Carlos (IQSC/BT) São Carlos.