Studies towards the synthesis of the guaianolide and pseudoguaianolide skeleton

De Kiss, Miklos (2012) Studies towards the synthesis of the guaianolide and pseudoguaianolide skeleton. Doctoral thesis, University of East Anglia.

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Abstract

A synthesis of the guaiane skeleton is presented in my thesis.
Guaianolides and pseudoguaianolides are sesquiterpene lactones and share a sommon
backbone: the guaiane skeleton. Hundreds of natural products belong to these families of
compounds. The guaiane skeleton is characterised by a bicyclo[5.3.0]decane ring system
(perhydroazulene). Among the guaianolide family, dehydroleucodine was chosen as a target
example.
The first part of the thesis introduces the guaianolide and pseudoguaianolide families. An
overview of the biological properties and the biosynthesis are reported. First, structures from
componds belonging to these families are described. Then, the biological properties of the
dehydroleucodine are reported and, finally, the syntheses of three sesquiterpene lactones are
shown.
The second part of the thesis reports my studies towards the synthesis of the guaiane
skeleton and dehydroleucodine. The key step of the construction of the perhydroazulene ring
system 3 is an intramolecular ene reaction. The lactone is build through an inversion of the
alcohol configuration followed by an allylic oxidation 2 and finished by an oxidation of the
primary alcohol 1. A proposal of the synthesis of dehydroleucodine is briefly explained.
The final part is the experimental part.
O
O
O
H
guaiane
dehydroleucodine
O
O
O
H
HO
H
H
O
HO
H
H
O
OH
H
H
O
O
O
1 2 3 4 5
Studies towards the Synthesis of the Guaianolide and Pseudoguaianolide skeleton.
iii
ACKNOWLEDGEMENTS
My studies were performed in Professor Page’s group at the University of East Anglia
(Norwich, Norfolk).
I would like to thank my supervisor, Professor Phil Page for his welcome in his laboratory
and the confidence Phil granted me for carrying on a subject started years ago.
Of course, I can’t forget my fiancée for her daily support through those hard times of
research, Doctor Yohan Chan for his help in the lab and outside, and all my lab-mates for the
nice atmosphere we work in.
I have a special thought to my so dear friend Franklin, who left us too early. I am sure he
would have loved to read this thesis through and give it his mark and corrections.
At last, I need to be grateful for the funding from the University of East Anglia.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Mia Reeves
Date Deposited: 13 Jun 2014 09:09
Last Modified: 13 Jun 2014 09:09
URI: https://ueaeprints.uea.ac.uk/id/eprint/48792
DOI:

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