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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 type:Scholarships in Brazil - Master
Effective date (Start): April 01, 2014
Effective date (End): July 31, 2016
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Antonio Carlos Bender Burtoloso
Grantee:Meire Yasuko Kawamura
Home 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


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)

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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. Web of Science Citations: 5.
Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
. 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.

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