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Title: An asymmetric Horner-Wittig reaction : synthesis of phytosterols and unravelling their role in disease
Author: Parry, Laura Jane
ISNI:       0000 0004 6057 7063
Awarding Body: University of Bradford
Current Institution: University of Bradford
Date of Award: 2014
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Phytosterol ; Horner-Wittig reaction ; Synthesis ; Disease mechanisms