Synthesis of single enantiomers of ω-1 methoxy mycolic acids from Mycobacterium alvei

Abstract

This thesis is discussed in three main parts. Firstly the synthesis of single enantiomers (R and S) of a ω-1 methoxy- cis-alkene-α-methyl trans-alkene mycolic acid (I, II), which have been isolated from M. alvei, an environmental mycobacterium, is described. This MA contains a methoxy group at the ω-1 position and two alkene groups in the mero chain, at the distal and proximal positions. The next part of the thesis describes the preparation of a number of sugar esters of mycolic acids (I and II). These include the TDM (III), TMM (IV), arabino-MA fragment from AG (V) and GMM (VI). The final part describes the synthesis of the specific cis-alkene-α-methyl-trans-alkene mycolic acid (VII), which has also been isolated from M. alvei. This MA contains a double bond at the distal and proximal positions. The preparation of mycolate esters, by esterification of this mycolic acid with trehalose to give TDM (VIII) and TMM (IX) is also discussed.