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Title: The total synthesis of vigulariol
Author: Hayes, Stewart
ISNI:       0000 0004 2669 6974
Current Institution: University of Nottingham
Date of Award: 2008
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(+)-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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available