
%0 Journal Article
%A Brimble, Margaret A. 
%A Davey, Roger M. 
%A McLeod, Malcolm D. 
%A Murphy, Maureen 
%T <emph type="2">C</emph>-Glycosylation of Oxygenated Naphthols with 3-Dimethylamino-2,3,6-trideoxy-<emph type="6">L</emph>-arabino-hexopyranose and 3-Azido-2,3,6-trideoxy-<emph type="6">D</emph>-arabino-hexopyranose
%J Australian Journal of Chemistry
%D 2003/07/18
%V 56
%N 8
%P 787-794
%K 
%R https://doi.org/10.1071/CH02236
%U https://www.publish.csiro.au/paper/CH02236 
%X In 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. 
