Towards the total synthesis of Ajudazol B

QD Chemistry

Adair, Liam David ; Marquez, Rudi

University:University of Glasgow

Department:School of Chemistry

关键词: Total synthesis, ajudazol B, organic chemistry.;   

Others  :  http://theses.gla.ac.uk/8711/1/2018AdairPhD.pdf

来源: University of Glasgow

【 摘 要 】

Ajudazol B is a polyketide secondary metabolite, isolated from Chondromyces crocatus in 2002, that exhibits anti-fungal activity through potent inhibition of the electron transport chain. The main objective of the work described in this thesis was to use and expand the oxidative rearrangement of isobenzofurans to generate isochromanones, and apply this towards the total synthesis of ajudazol B. The rearrangement was used as a key step in the synthesis of the full ajudazol B framework. The synthesis was achieved in 20 steps and 11% overall yield. The isomer of ajudazol B was synthesised in 21 steps and 8% overall yield. Its biological activity remains to be determined.