2134/33860
David C. Leach
David C.
Leach
Studies towards the synthesis of lactacystin
Loughborough University
2018
untagged
Chemical Sciences not elsewhere classified
2018-07-12 10:10:35
Thesis
https://repository.lboro.ac.uk/articles/thesis/Studies_towards_the_synthesis_of_lactacystin/9397811
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.]