Currie, Andrew Cochran
(1961)
14-hydroxycodeine and derivatives.
PhD thesis, University of Glasgow.
Full text available as:
Abstract
A series of 14-substituted codeine derivatives were prepared for pharmacological study by sodium borohydride reduction of the corresponding 14-hydroxy and 14-acyloxycodeinones. The epimeric 14-substituted isocodeines were not formed by this reaction but were prepared using 14-hydroxycodeine tosylate as an intermediate. The latter compound on treatment with 70% acetic acid gave the l4-hydroxyallopseudocodeine series. Lithium aluminium hydride reduction of 14-hydroxycodeine tosylate gave 14-hydroxydeoxycodeine and the very active analgesics, the 14-acyloxydeoxycodeines. Attempts to prepare known codeine derivatives from "hydroxy-codeine", the non-phenolic compound from the reaction of zinc dust and acetic acid on 14-hydroxycodeinone are described and a new structure is postulated. A new method is reported for the synthesis of 14-hydroxy-N-alkylnorcodeines. This involves the formation of 14-hydroxy-N-acylnorcodeine derivatives from the corresponding 14-acyloxy-N-cyano compound by acyl migration, and their reduction with lithium aluminium hydride.
Item Type: |
Thesis
(PhD)
|
Qualification Level: |
Doctoral |
Additional Information: |
Adviser: P L Pauson |
Keywords: |
Pharmacology |
Date of Award: |
1961 |
Depositing User: |
Enlighten Team
|
Unique ID: |
glathesis:1961-72537 |
Copyright: |
Copyright of this thesis is held by the author. |
Date Deposited: |
11 Jun 2019 11:06 |
Last Modified: |
11 Jun 2019 11:06 |
URI: |
http://theses.gla.ac.uk/id/eprint/72537 |
Actions (login required)
 |
View Item |