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Title: Formal synthesis of the asbestinin family of marine natural products
Author: Sigerson, Ralph Clark
ISNI:       0000 0004 2728 2773
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2012
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The asbestinins are a sub-class of the ether bridged 2,11-cyclised cembranoid family of marine natural products that have been isolated from octocoral species Briareum Asbestinum. They exhibit high structural complexity and a diverse range of bioactivities that include cytotoxicity against tumour cell lines, potent anti-bacterial properties and antagonism of both histamine and acetylcholine. This report presents the continued efforts in developing an efficient synthetic route to the asbestinins which will be general enough to enable the synthesis of virtually every member of this family of compounds. The key synthetic steps include; a samarium diiodide reductive cyclisation to generate 2,6-syn-5,6-anti tetrahydropyranol motif, oxonium ylide formation with subsequent [2,3]-sigmatropic rearrangement of a functionalised diazoketone and an intramolecular Diels-Alder cycloaddition to construct the cyclohexyl ring. Many studies have been carried out on other sub-classes within the ether bridged 2,11-cyclised cembranoid family of natural products, of particular interest have been the sarcodictyins and cladiellins, the latter of which has been extensively investigated within the Clark group.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry