Isopreneよりtrans-4-amino-1-hydroxy-2-methyl-2-buteneの合成 (2) (zeatinの合成)

概要

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The synthetic method of trans-4-amino-1-hydroxy-2-methyl-2-butene (7) constituting a partial structure of zeatin has been improved. The starting point for the present method was the abnormal addition of tert-butylhypochlorite to isoprene. The reaction of isoprene with tert-butylhypochlorite gave the mixture of trans-1-t-butoxy-4-chloro-2-methyl-2-butene (1) and trans-4-t-butoxy-1-chloro-2-methyl-2-butene (2) in 45% yields ((2)/(1)=1/3_??_4). An equivalent ammount of potassium phthalimide to (1) reacted with this mixture to give trans-1-t-butoxy-2-methyl-4-phthalimido-2-butene (5), predominantly. Compound (5) can be easily separated from the residue by the steam distillation of reaction mixture. The treatment of (5) with acetic anhydride-ferric chloride afforded trans-1-acetoxy-2-methyl-4-phthalimido-2-butene (6) followed by hydrolysis with barium hydroxide to give (7) in good yield.
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