Synthetic studies on the taxane diterpenoids
| dc.contributor.author | Phillips, Andrew John | en |
| dc.date.accessioned | 2012-12-02T21:21:02Z | |
| dc.date.available | 2012-12-02T21:21:02Z | |
| dc.date.issued | 1999 | en |
| dc.description.abstract | This thesis describes synthetic studies aimed towards developing a concise synthesis of taxinine, a member of the taxane class of natural products. In Chapter One, an overview of the strategies used for the synthesis of this class of compounds is provided. A bicyclic enone was identified as a target for the studies described in this thesis. The strategy described also called for the addition of the C-ring by ring-closing metathesis. A six step sequence to a C12-desmethyl A-ring is described in Chapter Two. The key step is the isomerization of an epoxide to an allylic alcohol. It was not possible to extend this chemistry to include C12-methylated substrates. An alternative Diels-Alder approach is also described. This approach allowed the synthesis of a number of C12-methylated A-ring structures. A concise synthesis of diene precursors suitable for exploring the possibility of RCM as a method for the ring closure to form a taxane AB-ring system is described in Chapter Three. The planned ring-closing metathesis reaction was unsuccessful under a number of conditions examined. An investigation described in Chapter Four delineates the use of ring-closing metathesis as a possible method for the introduction of the C-ring onto suitable AB-ring systems. An alternative to the unsuccessful ring-closing metathesis approach, an intramolecular Diels-Alder synthesis of a bicyclo[4.3.1]decene system, is described in Chapter Five. Preliminary investigations into the ring-expansion of this compound are also described. A brief summary and discussion of the future potential of the research conducted in this thesis is provided in Chapter Six. | en |
| dc.identifier.uri | http://hdl.handle.net/10092/7255 | |
| dc.identifier.uri | http://dx.doi.org/10.26021/8230 | |
| dc.language.iso | en | |
| dc.publisher | University of Canterbury. Chemistry | en |
| dc.relation.isreferencedby | NZCU | en |
| dc.rights | Copyright Andrew John Phillips | en |
| dc.rights.uri | https://canterbury.libguides.com/rights/theses | en |
| dc.title | Synthetic studies on the taxane diterpenoids | en |
| dc.type | Theses / Dissertations | |
| thesis.degree.grantor | University of Canterbury | en |
| thesis.degree.level | Doctoral | en |
| thesis.degree.name | Doctor of Philosophy | en |
| uc.bibnumber | 691380 | en |
| uc.college | Faculty of Science | en |
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