title: SmI2-mediated couplings of α-amino acid derivatives. Formal synthesis of (-)-pumiliotoxin 251D and (±)-epiquinamide.
abstract: The coupling between cyclic and acyclic α-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.
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil, and The School of Chemistry, University of Manchester , Manchester, M13 9PL, U.K.
authors: Vagner D
authors: VD
authors: Pinho
authors: David J
authors: DJ
authors: Procter
authors: Antonio C B
authors: AC
authors: Burtoloso
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C517877:8-hydroxy-8-methyl-6-(2'-methylhexylidene)-1-azabicyclo(4.3.0)nonane; D000179:Acrylates; D000596:Amino Acids; D007212:Indolizines; D007454:Iodides; D011807:Quinolizines; C481035:epiquinamide; D012493:Samarium; C409809:samarium diiodide; C035956:methyl acrylate