Formal synthesis of the asbestinin family of marine natural products

Sigerson, Ralph Clark (2012) Formal synthesis of the asbestinin family of marine natural products. PhD thesis, University of Glasgow.

Abstract

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.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Funded by EPSRC and GlaxoSmithKline.
• Keywords: Natural product, total synthesis, marine metabolite
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Clark, Prof. J. Stephen
• Date of Award: 4 December 2012
• Depositing User: Dr Ralph Clark Sigerson
• Unique ID: glathesis:2012-3835
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 09 Jan 2013 12:07
• Last Modified: 04 Dec 2015 13:14
• URI: https://theses.gla.ac.uk/id/eprint/3835