A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor |
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Authors: | Kate N Fanning |
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Institution: | WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK |
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Abstract: | A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H2-receptor, has been developed in 10 steps and in 31% overall yield from l-aspartic acid. The key steps involved a two-carbon homologation of an l-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. |
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Keywords: | Gizzerosine Gizzard erosion Amino acid synthesis Wittig reaction |
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