Synthesis of enantiopure carbo- and heterocyclic compounds from the products of benzoate dioxygenase

Abstract

Of the threats faced by current and future generations, man-made climate change is perhaps the greatest. In order to combat climate change, chemists must contribute to reducing the environmental impact of synthetic chemistry. Biocatalysis could be a useful tool with which to combat climate change, since environmentally benign syntheses of complex molecules can be achieved through its use.

Benzoate dioxygenase (BZDO) enzymes allow access to arene ipso,ortho-diols through the dearomatisation of sodium benzoate (scheme A-01). This enantiopure building block has previously shown utility in the synthesis of natural products and cyclitols.

This thesis sought to expand on the known chemistry of arene ipso,ortho-diol A-01 through the synthesis of arene diol derived heterocycles and asymmetric epoxidation organocatalysts (scheme A-01). In addition to these themes, the microbial oxidation of sodium 4-fluorobenzoate has been achieved, providing fluoro-arene ipso,ortho-diol A-02. The reactivity of fluoro-arene diol A-02 has been probed through a number of oxidative transformations.

Date of Award	19 Jun 2019
Original language	English
Awarding Institution	University of Bath
Supervisor	Tony James (Supervisor) & Simon Lewis (Supervisor)