Towards the first asymmetric total synthesis of (-)-Euonyminol
Author(s)
Webber, Matthew J.
Type
Thesis
Abstract
(–)-euonyminol is a poly-oxygenated sesquiterpene which was first isolated in 1953 by
Beroza. It was isolated by the saponification of a mixture of four alkaloids from
Tripterygium wilfordii Hook, a member of the Celastraceae plant family. Since its
discovery, (–)-euonyminol has been found to be a common core for a plethora of other
Celastraceae natural products. Among these are hypogluanine B and triptonine B, two
potent anti-HIV compounds.
In this thesis, an overview of the natural products of the Celastraceae is given,
highlighting euonyminol as a core of high value both in terms of biological activity and
as an intriguing synthetic target. The biological significance of the natural product class is
described with particular focus upon anti-HIV and multi-drug resistance reversal
properties. Prior synthetic work towards euonyminol and other molecules similar in
structure is also described.
The remainder of the thesis describes work carried out towards the total asymmetric
synthesis of (–)-euonyminol, employing a model system to develop chemistry suitable for
installing the southern hemisphere oxygenation pattern. Two synthetic routes are
described and both of these feature an Ireland-Claisen rearrangement as the key step.
Beroza. It was isolated by the saponification of a mixture of four alkaloids from
Tripterygium wilfordii Hook, a member of the Celastraceae plant family. Since its
discovery, (–)-euonyminol has been found to be a common core for a plethora of other
Celastraceae natural products. Among these are hypogluanine B and triptonine B, two
potent anti-HIV compounds.
In this thesis, an overview of the natural products of the Celastraceae is given,
highlighting euonyminol as a core of high value both in terms of biological activity and
as an intriguing synthetic target. The biological significance of the natural product class is
described with particular focus upon anti-HIV and multi-drug resistance reversal
properties. Prior synthetic work towards euonyminol and other molecules similar in
structure is also described.
The remainder of the thesis describes work carried out towards the total asymmetric
synthesis of (–)-euonyminol, employing a model system to develop chemistry suitable for
installing the southern hemisphere oxygenation pattern. Two synthetic routes are
described and both of these feature an Ireland-Claisen rearrangement as the key step.
Date Issued
2010
Date Awarded
2010-05
Copyright Statement
Attribution NoDerivatives 4.0 International Licence (CC BY-ND)
Advisor
Spivey, Alan
Sponsor
AstraZeneca
Creator
Webber, Matthew J.
Publisher Department
Chemistry
Publisher Institution
Imperial College London
Qualification Level
Doctoral
Qualification Name
Doctor of Philosophy (PhD)