A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H-2-receptor

Fanning, K. N. and Sutherland, A. (2007) A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H-2-receptor. Tetrahedron Letters, 48(48), pp. 8479-8481. (doi: 10.1016/j.tetlet.2007.09.165)

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 H-2-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. .

• Item Type: Articles
• Keywords: ACID ALPHA-AMINO-ACIDS amino acid synthesis AMINO-ACID ASPARTATE-SEMIALDEHYDE DEHYDROGENASE BROILER CHICKS DISEASE FACILE SYNTHESIS FISH-MEAL gizzard erosion gizzerosine INDUCER INHIBITORS STEP Wittig reaction
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: Fanning, K. N., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron Letters
• ISSN: 0040-4039