(+)-Vigulariol was isolated in 2005 by Sheu and coworkers off the coast of Taiwan and belongs to the cladiellin (eunicellin) class of the 2-11 cyclised cembranoid family of natural products. Vigulariol along with numerous other members of the cladiellin family have been shown to possess interesting biological properties including cytotoxicity against various cell lines. This thesis presents the total syntheses of (±)-vigulariol and (-)-vigulariol, that were completed in 20 steps respectively in an overall yield of 4.1% and 5.9%. The key steps in the synthesis are; a samarium diiodide reductive cyclisation to furnish a 2,6-syn-5,6-anti tetrahydropyranol, oxonium ylide formation and an intermolecular Diels-Alder cycloaddition to construct the cyclohexyl ring.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:495554 |
| Date | January 2008 |
| Creators | Hayes, Stewart |
| Publisher | University of Nottingham |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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