Issue 10, 2012

Pyrazinealkaloidsvia 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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
17 Nov 2011
Accepted
05 Jan 2012
First published
06 Jan 2012

Org. Biomol. Chem., 2012,10, 2126-2132

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

S. Badrinarayanan and J. Sperry, Org. Biomol. Chem., 2012, 10, 2126 DOI: 10.1039/C2OB06935K

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