| 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. | |
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MedLine Citation:
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PMID: 22293912 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Sandhya Badrinarayanan; Jonathan Sperry |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-2-1 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: - ISSN: 1477-0539 ISO Abbreviation: - Publication Date: 2012 Feb |
Date Detail:
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Created Date: 2012-2-1 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand. j.sperry@auckland.ac.nz. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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