Synthesis of an aromatic hydrocarbon diol epoxide–cytosine adduct, 5′-O-(9-phenylxanthen-9-yl)-N4-[(±)-1β,2α,3α-triacetoxy-1,2,3,4-tetrahydro-4β-naphthyl]-2′-deoxycytidine, suitable for incorporation into synthetic oligodeoxyribonucleotides

Abstract

The first total synthesis of a model polyaromatic hydrocarbon diol epoxide–cytosine adduct is described, suitable for incorporation into oligodeoxyribonucleotide synthesis. An approach to control the relative stereochemistry of the diol epoxide–nucleoside adduct is discussed. This synthesis yields 5′-O-(9-phenylxanthen-9-yl)-N⁴-[(±)-1β,2α,3α-triacetoxy-1,2,3,4-tetrahydro-4β-naphthyl]-2′-deoxycytidine as a mixture of diastereoisomers.