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Title: Studies towards the synthesis of the marine metabolite octalactin-A
Author: Howells, Garnet E.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1999
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Studies towards the synthesis of the two novel eight membered ring lactone natural products, the cytotoxic octalactin A 1 and octalactin B 2, will be described. (Fig. 10887A). The first part of this thesis discusses the methodology developed for the potential application to a total synthesis of 1 and 2. The key steps include; a boron mediate anti aldol coupling, an E-selective Horner Wadsworth Emmons coupling to give a tri-substituted double bond and a novel samarium-based cyclisation to produce several simple octalactin analogues containing unsubstituted rings (Chapter 2). The second part of this thesis describes an extension of the methodology developed to the stereoselective synthesis of racemic 3, a key fragment in the synthesis of the polyketide halichondramide (Chapter 3). (Fig. 10887B). Finally, the third part of the thesis outlines a synthetic route towards the octalactins based on the previously developed methodology. This includes the asymmetric synthesis of the two major aldehyde fragments 4 and 5 (Chapter 4).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available