The body of research in this thesis investigates the use of the Gallagher 3rd generation synthesis to make cytisine (i) and core variants of cytisine (ii) and (iii). A crucial step in the synthesis is the reduction of the lactam carbonyl, which can either be attempted before or after cyclisation. It was found that attempts to reduce the lactam carbonyl after cyclisation (iv) were unsuccessful, whereas reduction before cyclisation (v) was not reproducible. Alternative methodology to allow for the synthesis of a wider range of variants using a-arylation was developed. It was shown that the conditions used needed to be tailored to the system, making test systems not representative. By using a reduced number of equivalents of bromide in the reaction, diarylation, the main by-product isolated from a-arylation, could be supressed and only monoarylation (vi) was observed.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:658203 |
| Date | January 2014 |
| Creators | Smith, Charlotte Louise |
| Publisher | University of Bristol |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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