Extensive phytochemical studies carried out over the last two decades on plants of the genus <i>Illicium</i>, had led to the isolation and characterization of several anislactone-type sesquiterpenes. The neurotrophic activity of merrilactone A 17, coupled with the structural diversity which could be accessed by further derivatisation of other members, gives this family of secondary metabolites value in the process of discovering novel therapeutic agents to address the molecular causes underlying the progression of neurodegenerative diseases. Additionally, the anislactone-type sesquiterpenes family constitutes an ideal synthetic arena for the development of innovative methods dealing with the construction of highly-functionalised five-membered rings, and the creation of contiguous fully-substituted stereocentres. The thesis presented herein, describes the results obtained in the course of our investigations to lay the foundations of a synthetic program targeting the divergent total syntheses of several members of the anislactone-type sesquiterpenes family, including the novel implementation and limitations associated to a domino oxy-/carbopalladation reaction, which proved to be pivotal in the development of a short route towards the oxa[3.3.3]propellane carbocyclic core of merrilactone A, in addition to the development of a expeditive nine-steps route furnishing the tricyclic core of the anislactone-type sesquiterpenes 14, 15, 16 and 19, in a high overall yield.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:660532 |
| Date | January 2007 |
| Creators | Perea Buceta, Jesus E. |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/15628 |
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