Novel methodology towards the total synthesis of Pseudopterogorgia metabolites
thesisposted on 28.10.2013, 10:08 by Paul O'Hora
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.