Studies towards the synthesis of lactacystin

2018-07-12T10:10:35Z (GMT) by David C. Leach
This thesis contains three main chapters. The first chapter is a review of lactacystin and its derivatives including syntheses by other groups, biosynthesis and biological activity Chapter two contains work performed in our group and the final chapter reports the experimental details of the synthetic work. Our synthetic approach towards the synthesis of lactacystin includes a Dieckmann cyclisation of a suitable diester compound. This provides us the lactam core of the natural product. The diester compound can be formed by the condensation of N-protected glycine ethyl ester with a malonyl chloride. The C-3 methyl moiety was introduced by quenching the salt formed from the Dieckmann cyclisation. [Continues.]