Purines, pyrimidines, and imidazoles. Part XXIV. Syntheses of zeatin, a naturally occurring adenine derivative with plant cell-division-promoting activity, and its 9-β-D-ribofuranoside

Abstract

6-(4-Hydroxy-3-methylbut-trans-2-enylamino)purine (zeatin) a naturally occurring kinetin-like cell-division-promoting factor and its 9-β-D-ribofuranosyl derivative have been synthesised by reaction of trans-4-amino-2-methylbut-2-en-1-ol with 6-methylthiopurine (or 6-chloropurine) and 6-chloro-9-β-D-ribofuranosylpurine, respectively. The aminobutenol was prepared by reaction of methyl γ-bromotiglate with sodium azide and reduction of the resulting methyl γ-azidotiglate with lithium aluminium hydride. Some derivatives of the aminobutenol and zeatin, and the ozonisation of zeatin to methylglyoxal, are described.