6-(4-Hydroxy-3-methylbut-trans-2-enylamino)purine
(zeatin), a cytokinin isolated from Zea mays, has been synthesized by a new route. β- Methylcrotononitrile was brominated with N-bromosuccinimide
yielding γ- bromo-β-methylcrotononitrile,
from which trans-γ-acetoxy-β- methylcrotononitrile
was prepared. The alcohol derived from this acetate was converted into
trans-β-methyl-γ-(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 γ-alkoxy-β-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.
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