Thesis-2004-Allard.pdf (4.67 MB)
Novel approaches to the asymmetric synthesis of indole alkaloids
thesisposted on 2018-06-29, 11:02 authored by James E. Allard
The tetracyclic system (219) shares the same heterocyclic skeleton as a plethora of highly bioactive indole alkaloids, exemplified by ajmalicine (161) and deplancheine (204). [Illustration omitted.] Building on earlier work from our research group we recognised that a suitably substituted bicyclic lactam (266) could act as a precursor in an intramolecular N-acyliminium mediated cyclisation leading to targets such as (219). [Illustration omitted.] Methodology has been developed to remove the chiral auxiliary group. Manipulation of the template (219) has allowed us to achieve a novel total synthesis of deplancheine (208) and provided valuable insight for a future asymmetric synthesis of (204).
PublisherJames Edward Allard
Publisher statementThis 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/
NotesA Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.