Towards the synthesis of the ajudazols

Egan, Ben A. (2013) Towards the synthesis of the ajudazols. PhD thesis, University of Glasgow.

Abstract

The Ajudazols A and B are secondary metabolites, isolated in 2004 and exhibit anti-fungal and cytotoxic activity. The primary objective of the work presented in this thesis was to expand and develop our novel isobenzofuran oxidative rearrangement methodology for generation of isochromanones, and to apply this methodology towards the total synthesis of the ajudazols. An efficient, high yielding, regio- and diastereoselective oxidative rearrangement sequence has been developed, allowing for the generation of elaborately-functionalised isochromanone structures, from transient isobenzofuran intermediates. A flexible route to the synthesis of the ajudazol B eastern section was achieved, and this research culminated in the synthesis of ent-8-epi-ajudazol B.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Ajudazol, isobenzofuran, isochromanone, natural product, total synthesis
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Marquez, Dr. Rodolfo
• Date of Award: 2013
• Embargo Date: 9 May 2016
• Depositing User: Dr Ben Egan
• Unique ID: glathesis:2013-4259
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 13 May 2013 14:26
• Last Modified: 13 May 2016 14:04
• URI: https://theses.gla.ac.uk/id/eprint/4259