
TY  - JOUR
A1  - Brimble, Margaret A. 
A1  - Davey, Roger M. 
A1  - McLeod, Malcolm D. 
A1  - Murphy, Maureen 
T1  - <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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2003
VL  - 56
IS  - 8
SP  - 787
EP  - 794
KW  - 
UR  - https://doi.org/10.1071/CH02236 
N2  - 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. 
ER  -

