Total Synthesis of the Macroline-related Alkaloid (±)-Alstonerine
File(s)
Final Thesis
Author(s)
Pett, Richard
Type
Thesis
Abstract
This thesis examines the total synthesis of the macroline-related indole alkaloid alstonerine and related compounds. It is divided into three sections:
The first section provides a review of the total synthesis efforts reported by Cook, Martin, Kuethe, and Kwon, as well previous work within the Craig group.
The second section discusses the results of our investigations. The optimisation of the synthesis of key intermediate α,β-unsaturated lactam alcohol via directed-aziridine ring-opening is presented in detail. Our progress towards the synthesis of macroline-related alkaloids macroline, alstolactone, anhydromacrosalhine-methine and alstonerinal, as well as their N4-tosyl derivatives, from the key intermediate is discussed. The findings from these studies are presented en route to the total synthesis of alstonerine.
The third section contains experimental procedures and characterisation data for compounds synthesised.
The first section provides a review of the total synthesis efforts reported by Cook, Martin, Kuethe, and Kwon, as well previous work within the Craig group.
The second section discusses the results of our investigations. The optimisation of the synthesis of key intermediate α,β-unsaturated lactam alcohol via directed-aziridine ring-opening is presented in detail. Our progress towards the synthesis of macroline-related alkaloids macroline, alstolactone, anhydromacrosalhine-methine and alstonerinal, as well as their N4-tosyl derivatives, from the key intermediate is discussed. The findings from these studies are presented en route to the total synthesis of alstonerine.
The third section contains experimental procedures and characterisation data for compounds synthesised.
Version
Open Access
Date Issued
2013-04
Date Awarded
2013-11
Copyright Statement
Attribution NoDerivatives 4.0 International Licence (CC BY-ND)
Advisor
Craig, Donald
Sponsor
AstraZeneca (Firm)
Engineering and Physical Sciences Research Council
Publisher Department
Chemistry
Publisher Institution
Imperial College London
Qualification Level
Doctoral
Qualification Name
Doctor of Philosophy (PhD)