Deleterious effect of 7-methyl group on glycosylation of 2-naphthols

Add time:09/24/2019    Source:sciencedirect.com

C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (1). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols.

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