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.