C-Glycosylation of Oxygenated Naphthols with 3-Dimethylamino-2,3,6-trideoxy-L-arabino-hexopyranose and 3-Azido-2,3,6-trideoxy-D-arabino-hexopyranose

Margaret A. Brimble, Roger M. Davey, Malcolm D. McLeod and Maureen Murphy

Abstract

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.

Australian Journal of Chemistry 56(8) 787 - 794 (2003) doi:10.1071/CH02236