Total syntheses of the cardiotonics pumiliotoxin 209 F and homopumiliotoxin 223 G

• Grant number: 08/09653-9
• Support type: Scholarships in Brazil - Doctorate
• Effective date (Start): June 01, 2009
• Effective date (End): July 31, 2013
• Field of knowledge: Physical Sciences and Mathematics - Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Vagner Dantas Pinho
• Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated scholarship(s): 12/02367-6 - Total synthesis of the 209F pumiliotoxin alkaloid via SmI2 mediated cascade reaction, BE.EP.DR

Abstract

Pumiliotoxins (indolizidine alkaloids), homopumiliotoxins (quinolizidine alkaloids) 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. The development of multifunctional reagents for application in the synthesis of pumiliotoxins and homopumiliotoxins would permit the construction of these compounds in very quickly for biological studies regarding cardiotonic activity. With the aim to investigate the methodology for the preparation of both indolizidine and quinolizidine alkaloids described in the present project, employing those multifunctional reagents, the total syntheses of the cardiotonics pumiliotoxin 209 F and homopumiliotoxin 223 G will be accomplished. (AU)

Scientific publications

(4)

(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)

ROSSET, ISAC G.; DIAS, RAFAEL M. P.; PINHO, VAGNER D.; BURTOLOSO, ANTONIO C. B. Three-Step Synthesis of (+)-Preussin from Decanal. Journal of Organic Chemistry, v. 79, n. 14, p. 6748-6753, JUL 18 2014. Web of Science Citations: 15.

SGOBBI, LIVIA F.; PINHO, VAGNER D.; CABRAL, MURILO F.; BURTOLOSO, ANTONIO C. B.; MACHADO, SERGIO A. S. Hydrazone molecules as mimics for acetylcholinesterase. A new route towards disposable biosensors for pesticides?. SENSORS AND ACTUATORS B-CHEMICAL, v. 182, p. 211-216, JUN 2013. Web of Science Citations: 4.

PINHO, VAGNER D.; PROCTER, DAVID J.; BURTOLOSO, ANTONIO C. B. SmI2-Mediated Couplings of a-Amino Acid Derivatives. Formal Synthesis of (-)-Pumiliotoxin 251D and (+/-)-Epiquinamide. ORGANIC LETTERS, v. 15, n. 10, p. 2434-2437, MAY 17 2013. Web of Science Citations: 21.

BERNARDIM, BARBARA; PINHO, VAGNER D.; BURTOLOSO, ANTONIO C. B. alpha,beta-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D. Journal of Organic Chemistry, v. 77, n. 21, p. 9926-9931, NOV 2 2012. Web of Science Citations: 25.

Academic Publications

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

PINHO, Vagner Dantas. Diverted approaches to the synthesis of indolizidine alkaloids. 2013. Doctoral Thesis - Universidade de São Paulo (USP). Instituto de Química de São Carlos São Carlos.