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

Autor(es)

Pinho, Vagner D. ^[1] ; Procter, David J. ^[2] ; Burtoloso, Antonio C. B. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs - England

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 15, n. 10, p. 2434-2437, MAY 17 2013.
• Citações Web of Science: 21

Resumo

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)

• Processo FAPESP: 12/04685-5 - Novas metodologias sintéticas para a construção de sistemas pirrolidínicos, piperidínicos e indolizidínicos
• Beneficiário: Antonio Carlos Bender Burtoloso
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 08/09653-9 - Síntese total dos cardiotônicos pumiliotoxina 209 F e homopumiliotoxina 223 G
• Beneficiário: Vagner Dantas Pinho
• Modalidade de apoio: Bolsas no Brasil - Doutorado