Synthesis and Structure of the Marine Ascidian 8-Oxoadenine Aplidiamine

Abstract

Alkylation of 8-oxoadenosine (13) with 4-benzyloxy-3, 5-dibromobenzyl bromide (20), followed by Dimroth rearrangement and acid hydrolysis, provided N-(3, 5-dibromo-4-hydroxybenzyl)-8-oxoadenosine (15). The 2'-deoxy version of this reaction sequence accomplished the first synthesis of N-(3, 5-dibromo-4-hydroxybenzyl)-8-oxodenine (16), which is the correct expression for marine ascidian purine aplidiamine.