Stereocontrolled synthesis of a d-amicetose functionalised tetrahydroxanthone related to kigamicin A

A glycosylated tetrahydroxanthone mimicking the ABC subunit of kigamicin A is synthesised in five steps by a sequence that exploits a Pd catalysed C–O bond forming reaction to construct the tetrahydroxanthone nucleus; chemo- and enantioselective Ru-catalysed transfer hydrogenation to establish the C-14 hydroxyl stereochemistry in the A-ring; and a trichloroacetimidate activated donor to introduce the β-linked d-amicetose unit in a stereoselective manner.