Syntheses of the marine ascidian purine aplidiamine and its 9-β-D- ribofuranoside

Article abstract of DOI:10.1016/S0040-4039(98)00880-6

The title nucleoside 9 was synthesized by alkylation of 8-oxoadenosine (7) with 4-benzyloxy-3,5-dibromobenzyl bromide, followed by Dimroth rearrangement and acid hydrolysis. 2'-Deoxy version of this reaction sequence accomplished the first synthesis of aplidiamine (6).