A novel hetero Diels - Alder reaction has been developed to facilitate the
synthesis of annelated pyridines as models for pyridoacridine alkaloids.
The key reaction is based on an intramolecular Diels - Alder reaction of an aza
- 1,3-butadiene with an appropriate dienophile, to yield the desired annelated
An extension of this methodology is to exploit the Eglinton copper (IT)
dimerisation of terminal acetylenes. This allows for a unique double
intramolecular hetero Diels - Alder reaction, where four new rings are formed
in one step. This allows for a facile route to annelated bipyridines.
Ultimately this methodology has led to an approach to the total synthesis of the
natural product eilatin, a member of the class of compounds known as
A Doctoral Thesis. Submitted in partial fulfillment of the requirements for the award of Doctor of Philosophy of Loughborough University.