Studies on the total synthesis of polycyclic aromatic alkaloids

Francis Dhoro

Research output: ThesisDoctoral Thesis

Abstract

The thesis reports on synthetic studies directed at highly condensed heteroaromatic alkaloids. Chapter one details studies towards the total synthesis of alpkinidine. Two synthetic approaches involving cascade reactions were explored. The first, based on previous work, investigated the reactions of enolates and electrophilic quinonoid isoquinolinetriones. Difficulties in obtaining the necessary precursors led to this route being abandoned. The second approach sought to capitalise on the nucleophilicity of aminoquinones. A model cascade reaction that constructed the B and D of the pyrroloacridine ring-system was discovered. After considerable effort, the precursors required to apply this methodology to the synthesis of alpkinidine were obtained. However, the final cascade reaction did not succeed. Chapter two describes the total synthesis of perlolidine and its N-methyl derivative,via a β-selective Heck reaction of haloquinolines with butyl vinyl ether. These studies unequivocally proved the co-identity of perlolidine and samoquasine A and suggested that cherimoline is also perlolidine.
Original languageEnglish
QualificationDoctor of Philosophy
Awarding Institution
  • The University of Western Australia
Supervisors/Advisors
  • Piggott, Matthew, Supervisor
  • Koutsantonis, George, Supervisor
Thesis sponsors
Award date2 Dec 2019
DOIs
Publication statusUnpublished - 2019

Embargo information

  • Embargoed from 06/01/2020 to 06/01/2022. Made publicly available on 06/01/2022.

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