Use this URL to cite or link to this record in EThOS:
Title: Novel synthetic methodologies for the synthesis of heterocyclic rings
Author: Oswald, Magalie Florence
ISNI:       0000 0004 2724 7900
Awarding Body: University of Sussex
Current Institution: University of Sussex
Date of Award: 2010
Availability of Full Text:
Access from EThOS:
Access from Institution:
Part 1. Synthesis of Stereodefined Heterocyclic Rings. We wish to report the development of novel methodology for the synthesis of stereodefined heterocyclic rings, which could be used for the synthesis of natural products containing for example tetrahydrofuran motifs, such as members of the pamamycin family. Due to their ambivalent properties, organoaluminium reagents can easily react with acetals by transfering an alkyl group after prior coordination with the substrates. This work has led to the development of a novel cascade reaction. It involves the reaction of acetals with trialkylaluminium reagents, which is followed by a cyclisation reaction, generating consequently tetrahydrofuran or tetrahydropyran rings. In addition, investigation towards the synthesis of pyrrolidines was also carried out. Part 2. Investigation and Development of a Novel Cascade Reaction. The Bergman cycloaromatisation reaction is based on the formation of a biradical intermediate species and has been, over the years, a constant source of inspiration for scientists. Continued efforts over the last 40 years permitted, among other things, a better understanding of the mode of action of the enediyne antibiotics, a class of natural compounds with exceptional biological activities. The Parsons group recently developed a novel cyclisation reaction, which also generates a biradical species, and which could, after being trapped with a suitable alkene, lead to the formation of tricyclic molecules containing heterocyclic cores. As a result, we wish to further investigate this novel reaction and develop a tandem reaction, involving this reaction combined with a Diels-Alder reaction in order to generate pentacyclic molecules, in one synthetic operation, and from an acyclic precursor.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry