Thesis-2013-OHora.pdf (3.13 MB)
Novel methodology towards the total synthesis of Pseudopterogorgia metabolites
thesis
posted on 2013-10-28, 10:08 authored by Paul O'HoraIn 1982, routine screening of the Pseudopterogorgia elizabethae stirred the scientific community by showing the presence of cytotoxic metabolites with antimicrobial activity. Since this discovery a vast amount of research has been conducted in synthesising metabolites of the soft coral. Herein we report the developments towards the synthesis of two metabolites (+)-Erogorgiaene and (+)-Elisabethadione utilising three key reactions in setting up the molecules three chiral centres.
The use of asymmetric allylation, oxy-Cope rearrangement and cationic cyclisation was utilised to set up the desired stereocentres from a starting cinnamyl aldehyde. Natural elisabethadione was synthesised in a racemic form as a 2:1 mixture of diastereoisomers at the C-13 stereocentre.
Funding
Loughborough University
History
School
- Science
Department
- Chemistry
Publisher
© Paul O'HoraPublication date
2013Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.Language
- en