Syntheses Employing Acetylenic Precursors

Fraser, Matthew M (1954) Syntheses Employing Acetylenic Precursors. PhD thesis, University of Glasgow.

Abstract

A. Synthesis of Histamine. The allergenic agent histamine (4-2'-aminoethylglyoxaline) was prepared from but-2-yne-1:4-diol by a six-stage synthesis in high overall yield (41%) B. Structure of Carpaine. A key degradation product of the alkaloid carpaine had been previously formulated as 9-hydroxy-9-methltridecoic acid. This acid was synthesised by an unequivocal route and was found to possess physical and chemical properties radically different from those of the degradation product. This evidence confirms recent work that the structure of carpaine has been erroneously formulated. C. Synthetic Studies of Baikiain. (1:2:3:6-Tetrahydorpyridene-2-carboxylic acid. The amino acids 1:5-diamino-1-carboxypent-3(cis)-ene and 1-amino-1-carboxypent-3(cis)-en-5-ol were synthesised from but-2-yne-1:4-diol. It was expected that these amino acids would undergo ready ring closure, to produce baikiain, by elimination of ammonia and water respectively. All attempts at ring closure on the two amino acids, however, gave unchanged starting material or caused decomposition. D. Synthesis of 2-Deoxy-D,L-ribose. Starting from the commercially available but-2-yne-1:4-diol synthetic routes to this important sugar were extensively investigated. The best route was found to be via pentane-3:4:5-triol, hydorlyses of which with mild alkali gave syrupy 2-deoxy-D,L-ribose.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1954
• Depositing User: Enlighten Team
• Unique ID: glathesis:1954-79107
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 31 Mar 2020 09:09
• Last Modified: 31 Mar 2020 09:09
• URI: https://theses.gla.ac.uk/id/eprint/79107