Thesis-1995-Riddick.pdf (4.31 MB)
A novel hetero Diels - Alder reaction as a route to annelated pyridines and bipyridines
thesis
posted on 2012-10-08, 10:01 authored by David A. RiddickA 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.
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School
- Science
Department
- Chemistry
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© David A. RiddickPublication date
1995Notes
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.283327Language
- en
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Keywords
AcetylenesAlkynesAnnelated bipyridineAnnelated pyridineAza-l3-butadieneChiral bipyridineCyclisationDiels - AlderEglinton couplingEilatinIntramolecular Diels - AlderMarine alkaloidsMolecular modellingNatural productsPyridoacridineTerminal acetylenesTerminal alkynesChemical Sciences not elsewhere classified
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