
TY  - JOUR
A1  - Letham, DS 
A1  - Mitchell, RE 
A1  - Cebalo, T 
A1  - Stanton, DW 
T1  - Regulators of cell division in plant tissues. VII. The synthesis of zeatin and related 6-substituted purines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1969
VL  - 22
IS  - 1
SP  - 205
EP  - 219
KW  - 
UR  - https://doi.org/10.1071/CH9690205 
N2  - 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. 
ER  -

