Phytosterols are major components of food and are structurally related to cholesterol, but differ from it by virtue of a carbon substituent at the C-24 position and in some cases, a double bond between C-22 and C-23 (Figure i). Furthermore, phytosterols are shown to have protective actions against colon, breast, and prostate cancer1; further investigation is required as their mode of action is unknown. Thus, reported herein is the design and synthetic implementation required to construct these naturally occurring compounds. Figure i : Cholesterol Construction towards a double bond flanked by two asymmetric carbon atoms, observed in the phytosterol side chain, will be synthesised using an asymmetric Horner-Wittig (H-W) reaction, involving a chiral α-substituted aldehyde and a chiral β-substituted phosphine oxide. In addition to the synthesis, the stereochemical outcomes of these H-W reactions were probed. The results demonstrated, that by varying the steric bulk, electronic nature, and aromatic properties of the groups β to the phosphorus and α to the aldehyde can control the cis/trans selectivity in alkene formation. Finally, to display the utility of this methodology, the phytosterol compounds will be synthesised and tested in MD-MBA-231 cancer cell lines, allowing further investigation into the phytosterol mechanism of action.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:704888 |
| Date | January 2014 |
| Creators | Parry, Laura Jane |
| Publisher | University of Bradford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/10454/7565 |
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