Colchicine and Related Compounds

MacMillan, John (1949) Colchicine and Related Compounds. PhD thesis, University of Glasgow.

Abstract

A new synthesis of dibenzcycloheptatrienes has been developed. The method provides a route to derivatives unsymmetrically substituted in the lateral nuclei and is based upon the stepwise oxidation of the appropriate 9- or 10-methyl phenanthrenes. Thus 2:3:4:7-tetramethoxy-10-methyl phenanthrene has been oxidised to 9:12:13:14-tetramethoxy-3:4:5:6-dlbenzcyclohepta-1:3:5-trien-7-one which has been shown, by direct comparison, to be identical with a degradation product of colchicine, isolated by Barton, Cook and Loudon. Accordingly the dibenzcycloheptatriene structure of certain colchicine degradation products has been synthetically established. In an attempt to elucidate the aromatisation of colchiceine, the bromination of this primary hydrolysis product has been re-investigated. A weakly acidic bromo-derivative obtained in this manner is isomeric with tribromo-colchiceine and apparently distinct from the tribromo-carboxylic acid described by Windaus. Methylation of this compound has afforded a methyl ether (or ester), isomeric with tribromo-colchicine.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry.
• Colleges/Schools: College of Medical Veterinary and Life Sciences
• Supervisor's Name: Supervisor, not known
• Date of Award: 1949
• Depositing User: Enlighten Team
• Unique ID: glathesis:1949-79761
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 03 Mar 2020 10:38
• Last Modified: 08 Aug 2022 13:38
• Thesis DOI: 10.5525/gla.thesis.79761
• URI: https://theses.gla.ac.uk/id/eprint/79761