Thesis-2007-Gaskell.pdf (13.21 MB)
Novel synthetic applications of N-acyliminium ions toward β-turn mimetics and naturally occurring alkaloids
thesis
posted on 2018-08-08, 08:39 authored by Sean N. GaskellThe asymmetric approach to a range of substituted indolizidine templates (3) from nonracemic
substrates (1), based around the development of a diastereoselective
N-acyliminium cyclisation strategy, is well established within our group. [Illustration omitted.] The application of this novel methodology in target synthesis has been demonstrated by
the manipulation of chiral building blocks such as (3). The removal of functional
groups has allowed assess to therapeutically active natural products including
(+)-crispine A (4) and (+)-harmicine (5), whilst the exploitation of their existing
functionality has been utilized to form complex β-turn peptide mimics, such as (6). [Illustration omitted.] The scope of this methodology has been extended with the novel N-acyliminium
cyclisation/retro Diels–Alder tandem synthesis of the complex pentacyclic template
(10), from the lactam precursor (9). Analogues of such templates are used as key
intermediates in the synthesis of the Cephalotaxus alkaloids.
Funding
Loughborough University. GlaxoSmithKline plc.
History
School
- Science
Department
- Chemistry
Publisher
© Sean Nicholas GaskellPublisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2007Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en