
%0 Journal Article
%A Letham, DS 
%A Mitchell, RE 
%A Cebalo, T 
%A Stanton, DW 
%T Regulators of cell division in plant tissues. VII. The synthesis of zeatin and related 6-substituted purines
%J Australian Journal of Chemistry
%D 1969/01/01
%V 22
%N 1
%P 205-219
%K 
%R https://doi.org/10.1071/CH9690205
%U https://www.publish.csiro.au/paper/CH9690205 
%X 6-(4-Hydroxy-3-methylbut-trans-2-enylamino)purine (zeatin), a cytokinin isolated from Zea mays, has been synthesized by a new route. &#946;- Methylcrotononitrile was brominated with N-bromosuccinimide yielding &#947;- bromo-&#946;-methylcrotononitrile, from which trans-&#947;-acetoxy-&#946;- methylcrotononitrile was prepared. The alcohol derived from this acetate was converted into trans-&#946;-methyl-&#947;-(tetrahydropyran-2- yloxy)crotononitrile. Reduction and acid hydrolysis gave 4-amino-2- methylbut-trans-2-en-1-ol which was made to react with 6-chloropurine to yield zeatin.     Several &#947;-alkoxy-&#946;-methylcrotononitriles were prepared and reduced by aluminium chloride-lithium aluminium hydride to the corresponding unsaturated amines. Saturated nitrile formation also occurred in these reductions. The amines prepared were condensed with 6-chloropurine to yield a series of O-alkylzeatins. A number of other zeatin analogues were also synthesized. Two 6-methoxyalkylamino-purines were cleaved by sodium borohydride in the presence of iodine to 6-hydroxy- alkylaminopurines. 
