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Thesis-1995-Riddick.pdf (4.31 MB)

A novel hetero Diels - Alder reaction as a route to annelated pyridines and bipyridines

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thesis
posted on 2012-10-08, 10:01 authored by David A. Riddick
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 pyridine. 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 pyridoacridines.

History

School

  • Science

Department

  • Chemistry

Publisher

© David A. Riddick

Publication date

1995

Notes

A Doctoral Thesis. Submitted in partial fulfillment of the requirements for the award of Doctor of Philosophy of Loughborough University.

EThOS Persistent ID

uk.bl.ethos.283327

Language

  • en