Brimble, Margaret ADavey, Roger MMcLeod, MalcolmMurphy, Maureen2015-12-100004-9425http://hdl.handle.net/1885/53334In connection with studies directed towards the synthesis of the pyranonaphthoquinone antibiotic medermycin, C-aryl glycosides were prepared by C-glycosylation of naphthols with glycosyl donors. Boron trifluoride diethyl etherate proved to be a suitable Lewis acid to promote the C-glycosylation, and use of the azido glycosyl donor proved more successful than using the dimethylamino glycosyl donor. 5-Hydroxy-1,4-dimethoxynaphthalene underwent facile C-glycosylation with two particular glycosyl donors, whereas 3-bromo-5-hydroxy-1,4-dimethoxynaphthalene was not an effective coupling partner with the same glycosyl donors. These studies indicate that subtle steric and electronic effects need to be considered in order to fine-tune C-glycosylations when using highly functionalized glycosyl donors.Keywords: Addition reactions; Boron compounds; Naphthalene; Nuclear magnetic resonance spectroscopy; Oxidation; Structure (composition); Synthesis (chemical); Boron trifluoride diethyl etherate; Dimethylamino glycosyl; Glycosylation; Hydroxydimethoxynaphthalene; Le200310.1071/CH022362015-12-09