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.
L. B. Davies, S. G. Greenberg and P. G. Sammes, J. Chem. Soc., Perkin Trans. 1, 1981, 1909 DOI: 10.1039/P19810001909
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