SmI2-Mediated Couplings of α-Amino Acid Derivatives. Formal Synthesis of (−)-Pumiliotoxin 251D and (±)-Epiquinamide

descriptionPublicationkeyboard_double_arrow_right Article 02 May 2013 English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 15, pages 2,434-2,437 (issn: 1523-7060, eissn: 1523-7052,

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Authors: Vagner D, Pinho; David J, Procter; Antonio C B, Burtoloso;

doi: 10.1021/ol400903n

pmid: 23639065

SmI2-Mediated Couplings of α-Amino Acid Derivatives. Formal Synthesis of (−)-Pumiliotoxin 251D and (±)-Epiquinamide

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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.

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Keywords

Samarium, Acrylates, Molecular Structure, Indolizines, Stereoisomerism, Amino Acids, Iodides, Quinolizines

13 Research products, page 1 of 2

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