Use this URL to cite or link to this record in EThOS:
Title: A novel hetero Diels-Alder reaction as a route to annelated pyridines and bipyridines
Author: Riddick, David A.
ISNI:       0000 0001 3518 2762
Awarding Body: Loughborough University of Technology
Current Institution: Loughborough University
Date of Award: 1995
Availability of Full Text:
Access from EThOS:
Access from Institution:
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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Acetylenes ; Alkynes ; Annelated bipyridine ; Annelated pyridine ; Aza-l ; 3-butadiene ; Chiral bipyridine ; Cyclisation ; Diels - Alder ; Eglinton coupling ; Eilatin ; Intramolecular Diels - Alder ; Marine alkaloids ; Molecular modelling ; Natural products ; Pyridoacridine ; Terminal acetylenes ; Terminal alkynes