Synthesis of 3-β-D-ribofuranosylwybutine, the most probable structure for the hypermodified nucleoside isolated from yeast phenylalanine transfer ribonucleic acids

Abstract

An alternative synthesis of the key intermediate 8 for the synthesis of wybutine 1 has been attained through the Heck reaction between (S)-N-(methoxycarbonyl)vinylglycine 13 and 1-benzyl-7-iodowye 7. The nucleoside version of this method using 7-iodo-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)wye 19, followed by catalytic hydrogenation, afforded a mixture of diastereoisomers 22 and 23. Separation of isomer 22 by means of high-performance liquid chromatography, followed successively by esterification and deprotection has accomplished the first synthesis of 3-(β-D-ribofuranosyl)wybutine 3, which is the most probable structure for wybutosine isolated from phenylalanine transfer ribonucleic acids.