Literature methods for the synthesis of benzyl 6-oxo-penicillanate have been studied, it was apparent that some of these reports contained conflicting information with regards to reaction conditions and yields. The same methodology was also used to synthesise the cephalosporin analogue <i>t</i>.butyl7-oxocephalosporanate. The reactions of these compounds with various trimethylsilyl amides and with the Wittig reagent 5'triphenylphosphoranylidenecyclohexanespiro-2'-(1',3'dioxolan)-4'-one have been investigated. The potential for attaching penicillin and cephalosporin nuclei to polymer supports, and thereby utilising the well developed methodology of solid phase peptide synthesis in the field of the discovery of novel β-lactam compounds, has been investigated. Difficulties were encountered when attempting to remove the β-lactams from the resin, however both penicillin and cephalosporin compounds were recovered, in low yield, having had the 6β-(7β-) amino protecting group changed whilst attached to the resin.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:653984 |
| Date | January 1992 |
| Creators | Lloyd, Christopher T. |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/15227 |
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