Synthesis of (±)-actinidine by an intramolecular cycloaddition process

Abstract

A new synthesis of (±)-actinidine (1), which relies on intramolecular cycloaddition of an acetylene across a pyrimidine ring, is described. Preparation of 5-(hept-5-yn-2-yl)-4,6-dihydroxypyrimidine (2) followed by thermolysis afforded 1-hydroxyactinidine (13), which could be converted into (±)-actinidine by chlorination and hydrogenation.