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Please use this identifier to cite or link to this item: https://dspace.lboro.ac.uk/2134/13437

Title: Novel methodology towards the total synthesis of Pseudopterogorgia metabolites
Authors: O'Hora, Paul
Keywords: Pseudopterosin
Erogorgiaene
elisabethadione
Colombiasin A
Asymmetric allylation
Oxy-Cope
Cationic cyclisation and natural product synthesis
Issue Date: 2013
Publisher: © Paul O'Hora
Abstract: 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.
Description: A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.
Sponsor: Loughborough University
URI: https://dspace.lboro.ac.uk/2134/13437
Appears in Collections:PhD Theses (Chemistry)

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