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Title: A novel hetero Diels - Alder reaction as a route to annelated pyridines and bipyridines
Authors: Riddick, David A.
Keywords: Acetylenes
Annelated bipyridine
Annelated pyridine
Chiral bipyridine
Diels - Alder
Eglinton coupling
Intramolecular Diels - Alder
Marine alkaloids
Molecular modelling
Natural products
Terminal acetylenes
Terminal alkynes
Issue Date: 1995
Publisher: © David A. Riddick
Abstract: 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.
Description: A Doctoral Thesis. Submitted in partial fulfillment of the requirements for the award of Doctor of Philosophy of Loughborough University.
URI: https://dspace.lboro.ac.uk/2134/10591
Appears in Collections:PhD Theses (Chemistry)

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