Towards the total synthesis of Ajudazol B

Adair, Liam David (2017) Towards the total synthesis of Ajudazol B. PhD thesis, University of Glasgow.

Abstract

Ajudazol B is a polyketide secondary metabolite, isolated from Chondromyces crocatus in 2002, that exhibits anti-fungal activity through potent inhibition of the electron transport chain.

The main objective of the work described in this thesis was to use and expand the oxidative rearrangement of isobenzofurans to generate isochromanones, and apply this towards the total synthesis of ajudazol B. The rearrangement was used as a key step in the synthesis of the full ajudazol B framework. The synthesis was achieved in 20 steps and 11% overall yield.

The isomer of ajudazol B was synthesised in 21 steps and 8% overall yield. Its biological activity remains to be determined.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Total synthesis, ajudazol B, organic chemistry.
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Marquez, Prof. Rudi
• Date of Award: 2017
• Depositing User: Dr. Liam David Adair
• Unique ID: glathesis:2017-8711
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2018 15:10
• Last Modified: 09 Mar 2018 09:36
• URI: https://theses.gla.ac.uk/id/eprint/8711