Use this URL to cite or link to this record in EThOS:
Title: Cascade cyclisation reactions and their application toward the synthesis of lactonamycin
Author: Jones, Daniel Ross
ISNI:       0000 0004 7223 7306
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2018
Availability of Full Text:
Access from EThOS:
Access from Institution:
The lactonamycins represent a class of natural products which possess significant biological activity with high potencies in cancer cell lines and against multi-drug resistant strains of bacterial infections. Here, a cascade cyclisation, developed in the Parsons group, has been used in the synthesis of the pentacyclic core of lactonamycin. The thermal cyclisation of an ene-diyne allows for a transition metal free synthesis of five of the six rings of lactonamycin in ten synthetic steps. Studies on the functionalisation of the pentacyclic core of lactonamycin have also been undertaken. A proposed strategy for the completion of the total synthesis has also been outlined. In addition, a novel method for the synthesis of highly substituted aromatic rings has been discovered in the Parsons group. This reaction involves the thermal opening of a furan ring which is induced by the ring closing reaction of a diyne / Diels-Alder cascade. This provides penta- and hexa-substituted aromatic rings with potential pharmaceutical applications as templates for drug design. Some palladium-mediated cascade cyclisation methodology of similar, alkenyl bromide analogues is also discussed.
Supervisor: Parsons, Philip Sponsor: Engineering and Physical Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral