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

概要

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The synthesis of trans-4-amino-1-hydroxy-2-methyl-2-butene (7) constituting a partial structure of zeatin has been extensively studied. The reaction of isoprene with tert-butylhypochlorite in acetic acid gave trans-4-acetoxy-1-chloro-2-methyl-2-butene (1) followed by hydrolysis with barium hydroxide to afford trans-1-chloro-4-hydroxy-2-methyl-2-butene (2). Compound (2) reacted with benzyltrimethylammonium benzoate and benzyltrimethylammonium acetate to give the corresponding trans-1-benzoyloxy-4-hydroxy-2-methyl-2-butene (3) and trans-1-acetoxy-4-hydroxy-2-methyl-2-butene(3), respectively. The bromination of (3) and (3) with phosphorus tribromide afforded trans-1-benzoyloxy-4-bromo-2-methyl-2-butene (4) and trans-1-acetoxy-4-bromo-2-methyl-2-butene (4) which were treated with potassium phthalimide to give the corresponding trans-1-benzoyloxy-2-methyl-4-phthalimido-2-butene (5) and trans-1-acetoxy-2-methyl-4-phthalimido-2-butene (5), respectively. The hydrolysis of (5) and (5) with barium hydroxide gave (7) in good yield.
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