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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

SmI2-Mediated Couplings of a-Amino Acid Derivatives. Formal Synthesis of (-)-Pumiliotoxin 251D and (+/-)-Epiquinamide

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Author(s):
Pinho, Vagner D. [1] ; Procter, David J. [2] ; Burtoloso, Antonio C. B. [1]
Total Authors: 3
Affiliation:
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs - England
Total Affiliations: 2
Document type: Journal article
Source: ORGANIC LETTERS; v. 15, n. 10, p. 2434-2437, MAY 17 2013.
Web of Science Citations: 21
Abstract

The coupling between cyclic and acyclic a-amino acid derivatives and methyl acrylate, mediated by samarium diiodide, is described. The method constitutes a powerful tool to construct indolizidine, quinolizidine, and piperidine systems in a straightforward two-step fashion. The formal synthesis of (-)-pumiliotoxin 251D and (+/-)-epiquinamide is achieved after two or three steps from these amino acid derivatives. (AU)

FAPESP's process: 08/09653-9 - Total syntheses of the cardiotonics pumiliotoxin 209 F and homopumiliotoxin 223 G
Grantee:Vagner Dantas Pinho
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 12/04685-5 - New synthetic methodologies for the construction of pyrrolidine, piperidine and indolizidine systems
Grantee:Antonio Carlos Bender Burtoloso
Support type: Regular Research Grants