A convergent route towards marine polycyclic ethers via a novel centrosymmetric approach

Martin, Emily (2025) A convergent route towards marine polycyclic ethers via a novel centrosymmetric approach. PhD thesis, University of Glasgow.

Abstract

Marine ladder polyether (MLP) toxins are a family of toxins produced by various dinoflagellates species. These natural products exhibit a wide array of toxic and pharmaceutical effects. Their complex structures and potentially useful bioactivities make them an attractive total synthesis target. Previous total syntheses of the MLP toxins suffer from large step counts and low overall yields, which presents a challenge for investigating their biological effects.

This project exploit the hidden symmetry within the MLP toxins. This project demonstrates a bidirectional synthetic approach to MLP toxins with a key desymmetrisation step in order to diverge fragments when necessary. This bidirectional approach increases synthetic efficiency by decreasing overall step count.

This thesis focuses on two main aims; attempts towards the total synthesis of gymnocin B, and the synthesis of various MLP fragments. A convergent bidirectional route to gymnocin B has been developed and efforts have been made at its completion. To fully demonstrate the versatility of this approach, fragments from an assortment of MLPs have been synthesised from a single key symmetric intermediate.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Clark, Professor J. Stephen
• Date of Award: 2025
• Depositing User: Theses Team
• Unique ID: glathesis:2025-85174
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 10 Jun 2025 15:36
• Last Modified: 10 Jun 2025 15:39
• Thesis DOI: 10.5525/gla.thesis.85174
• URI: https://theses.gla.ac.uk/id/eprint/85174