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Synlett 1991; 1991(10): 715-716
DOI: 10.1055/s-1991-34773
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First Synthesis of Theonellin Isocyanide

Yoshiyasu Ichikawa*
  • *Faculty of Education, Mie University, Tsu, Mie 514, Japan
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Publication Date:
13 March 2002 (online)

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Biomimetic synthesis of theonellin isocyanide (1; 4-[(1E,3E)-1,5-dimethyl-1,3-hexadienyl]-1-isocyano-1-methylcyclohexane) has been achieved by employing the triflic acid promoted Ritter type raction with acetonitrile at low temperature (-78 °C) to convert a 4-substituted 1-methylcyclohexene into the corresponding 1-acetamido-1-methylcyclohexane. Julia trans olefination was employed to construct the diene moiety.