Underexploited (ipso, ortho) Microbial Arene Dihydroxylation
: Uses in Synthesis & Catalysis

  • Julia Griffen

Student thesis: Doctoral ThesisPhD

Abstract

This thesis sought to expand upon the synthetic application of the underexploited ipso, ortho diene cis-diol microbial arene oxidation product from benzoic acid. The microbial oxidation of benzoic acid by mutant strains of bacteria to give the ipso, otho diene cis-diol may be considered to be a green and clean method. This biocatalytic route yields large quantities of an enantiopure chiral building block, which is not assessable via traditional synthetic methods. The fermentation product has seen application towards the synthesis of aminocylitols, which have been tested for their biological activity. Attempts to synthesise the fully oxygenated counterparts, cyclitols, were investigated. Expansion of previous work using a bromine substituted derivative led to a range of cross-coupled and iron co-ordinated products. Finally, a range of novel chiral acids and ketones were synthesised and evaluated for their catalytic activity towards asymmetric epoxidation.
Date of Award22 Nov 2013
Original languageEnglish
Awarding Institution
  • University of Bath
SupervisorSimon Lewis (Supervisor) & Tom Arnot (Supervisor)

Keywords

  • microbial arene oxidation
  • asymmetric catalysis
  • asymmetric synthesis
  • Fermentation
  • epoxidation
  • dihydroxylation
  • stereoselective catalysis
  • azacarbasugars
  • inositols
  • cyclitols
  • aminocarbasugars

Cite this

Underexploited (ipso, ortho) Microbial Arene Dihydroxylation: Uses in Synthesis & Catalysis
Griffen, J. (Author). 22 Nov 2013

Student thesis: Doctoral ThesisPhD