title: Pyrazine alkaloids via dimerization of amino acid-derived α-amino aldehydes: biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3-indolylmethyl)pyrazine and actinopolymorphol C.
abstract: The dimerization of amino acid-derived α-amino aldehydes provides a short, biomimetic synthesis of several 2,5-disubstituted pyrazine natural products. The α-amino aldehyde intermediates were generated in situ by the hydrogenolysis of their Cbz-derivatives. It was found that a judicious choice of reaction solvent facilitated hydrogenolysis, dimerization and oxidation to the natural product in a one-pot operation. This methodology demonstrates the viability of a recently proposed, alternative biosynthetic route to 2,5-disubstituted pyrazines in nature. Furthermore, this work describes a novel, concise approach to pyrazines from α-amino aldehydes derived from readily available, cheap amino acids.
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Sandhya
authors.initials: S
authors.lastname: Badrinarayanan
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sperry
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D032701:Biomimetics; D019281:Dimerization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C471671:2,5-bis(3-indolylmethyl)pyrazine; D000447:Aldehydes; D000470:Alkaloids; D000596:Amino Acids; D007211:Indoles; D011719:Pyrazines