Studies towards the total synthesis of manzamine A

Alharbi, Hibah Saeed (2022) Studies towards the total synthesis of manzamine A. PhD thesis, University of Glasgow.

Abstract

Manzamine A was isolated from a marine sponge of the genus Haliclona by Higa and coworkers in 1986.8 The structure of manzamine A consists of complicated 5-, 6-, 6-, 8-, and 13-membered rings, two tertiary amines and a tertiary alcohol functionality, in addition to a β-carboline. The synthetically challenging structure and the extremely potent biological activity of manzamine A makes it an attractive synthetic target.

Previous work in the Clark group had established the ring expansion of the tetracyclic ketone, which served as the key intermediate in the total synthesis of nakadomarin A published by the group in 2016.

In this thesis, the initial focus was towards optimization of the synthesis of the tetracyclic ketone. The second part was exploring the ring expansion of the tetracyclic advanced intermediate via different strategies. Finally, work was carried out towards the elaboration of the ring expanded tetracyclic ketone to give the functionalised ring expanded 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 Stephen J.
• Date of Award: 2022
• Depositing User: Theses Team
• Unique ID: glathesis:2022-83099
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 31 Aug 2022 11:17
• Last Modified: 31 Aug 2022 11:20
• Thesis DOI: 10.5525/gla.thesis.83099
• URI: https://theses.gla.ac.uk/id/eprint/83099