Use this URL to cite or link to this record in EThOS: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.780722
Title: Oxonium ions, rearrangements, and natural products
Author: Chan, Hau Sun
ISNI:       0000 0004 7966 3623
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2019
Availability of Full Text:
Access from EThOS:
Full text unavailable from EThOS. Restricted access.
Access from Institution:
Abstract:
This thesis focuses on the studies of a set of biologically relevant oxonium ions pertinent to the natural product biosynthesis of the red algae of the genus Laurencia. The total synthesis of these oxonium ions is reported along with their structural elucidation supported by extensive NMR spectroscopic analysis and DFT computations. The biosynthetic significance of these oxonium ions is demonstrated by their direct derivatisation into 12 natural products, namely (Z/E)-bromofucins, (Z/E)-chlorofucins, (Z/E)-elatenynes, laurendecumenyne B, laurefurenyne E, laurefurenyne F, ent-(Z/E)-laurefucins and ent-acetyllaurefucin. Furthermore, 6 additional natural products are synthesised indirectly from the oxonium ions, namely (Z/E)-notoryne, laurefurenyne C, laurefurenyne D, ent-deacetyllaurencin and ent-laurencin. The total synthesis of laurefurenynes C-F also enabled their structural reassignment. Chapters 1-3 of this thesis introduce the project, provide a brief summary of the chemistry of oxonium ions, and an overview of the proposed biosyntheses of Laurencia natural products. Chapters 4-6 report the total synthesis of the oxonium ions, their characterisation and their direct derivatisation into various natural products. Chapters 7-8 concerns the total synthesis of ent-deacetyllaurencin, ent-laurencin and the total synthesis of laurefurenyne C-F and their structural reassignment.
Supervisor: Burton, Jonathan Sponsor: Croucher Foundation
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.780722  DOI: Not available
Keywords: Chemistry, Organic
Share: