Studies Towards The Novel Synthesis Of Benzoisochromane Quinone Polyketides

Granaticin is a structurally unique member of the benzoisochromane quinone (BIQ) family of antibiotics. The molecule and its derivative exhibit a sugar moiety fusted to the naphthazarin core, only exhibited by one other natural compound, by a C-C glycosidic bond and an aldol like bond. The mechanism of enzymatic attachment of this substituent is currently unknown. This project aimed to devise a novel and elegant synthesis towards the granaticin aglycone and other benzoisochromane quinone natural compounds with the long term aim of discerning the mechanism of glycosylation. This thesis shows a novel route for the synthesis of highly substituted isochromane and isochromane quinone compounds towards the eventual synthesis of the desired natural molecules.

Name dc:type.qualificationname

phd

Level dc:type.qualificationlevel

doctoral

Grantor dc:publisher.institution

University of East Anglia

Year dc:date.issued

2014

Author dc:creator

• McGaw, Oliver

Language dc:language

en