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Title: Novel methodology towards the total synthesis of Pseudopterogorgia metabolites
Author: O'Hora, Paul
Awarding Body: Loughborough University
Current Institution: Loughborough University
Date of Award: 2013
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In 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.
Supervisor: Not available Sponsor: Loughborough University
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Pseudopterosin ; Erogorgiaene ; elisabethadione ; Colombiasin A ; Asymmetric allylation ; Oxy-Cope ; Cationic cyclisation and natural product synthesis