Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 10, Pages 2126-2132Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob06935k
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The dimerization of amino acid-derived alpha-amino aldehydes provides a short, biomimetic synthesis of several 2,5-disubstituted pyrazine natural products. The alpha-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 alpha-amino aldehydes derived from readily available, cheap amino acids.
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