The synthesis of mycolic acids

This project consists of three parts. In the first part the synthesis of two mycolic acid diastereomers (I and II) was achieved, thereby completing the full range of the cisdicyclopropane a-mycolic acid diastereomers. The second part comprised the development of a new method for the synthesis of the a-alkyl-B-hydroxy fragment of mycolic acids; two novel routes that involved fewer steps ted using L-malic as starting material. The first route which was via diethyl malate was achieved in fewer steps without a significant reduction in percentage yield. The second route via dimethyl malate was also completed successfiilly. Finally, a model cord facto III of a B-hydroxy carboxylic acid without an a-alkyl chain was prepared.EThOS - Electronic Theses Online ServiceGBUnited Kingdo