Thesis-2008-Duffy.pdf (5.8 MB)
Novel synthetic routes towards polycyclic alkaloids and tetracycline ring systems
thesis
posted on 2018-08-21, 09:17 authored by Liam J. DuffyNovel and complementary routes for the selective preparation of either the 2,11 b-cis (B)
or trans (C) series of functionalised benzo[α]quinolizidines have been developed and
reported in close collaboration with the Bosch group. The common aromatic core, chiral
p-aminoalcohol (A), allows access to either (B) or (C) via judicious choice of substrate
sub-structure for lactamisation. The key cyclisation step in both instances involves the
attack of a pendent aromatic nucleophile onto an N-acyliminium intermediate. [Illustration omitted.] Also described in this thesis is the first asymmetric synthesis of the
dodecahydrobenz[α]indolo[3,2-h]quinolizine ring system (E), a common sub-structure of
several bioactive indole alkaloids. Our approach furnishes the pentacyclic indole core of
the manadomanzamine skeleton with complete control over the relative and absolute
stereochemistries at the three contiguous chiral centres at positions 1, 10 and 24. [Illustration omitted.] The source of indole and chiral auxiliary, (S)-tryptophanol (D) has also been elaborated
towards a functionalised analogue (F) with a synthetic 'handle' for further derivatisation.
Synthetic routes towards the tetracycline class of compounds have also been investigated.
History
School
- Science
Department
- Chemistry
Publisher
© Liam John DuffyPublisher 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
2008Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en