Synthesis of 6-(4,5-dihydrofuran-2-yl)- and 6-(tetrahydrofuran-2-yl)purine bases and nucleosides

Abstract

A novel approach to the synthesis of purine derivatives (bases and nucleosides) bearing 4,5-dihydrofuran-2-yl and tetrahydrofuran-2-yl substituents at the 6-position as partly and fully saturated analogues of biologically active 6-hetarylpurine nucleosides is reported. Palladium-catalyzed cross-coupling reactions of 6-iodopurines with new (4,5-dihydrofuran-2-yl)zinc chloride (1) gave 6-(4,5-dihydrofuran-2-yl)-purines in high yields. Their catalytic hydrogenation gave 6-(tetrahydrofuran-2-yl)purines. These modified purine bases and nucleosides did not exhibit any significant cytostatic or anti-HCV activity. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.