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Synthesis 1988; 1988(12): 970-972
DOI: 10.1055/s-1988-27770
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A Simple Synthesis of Erbstatin and Its cis-Isomer

J. Kleinschroth* , J. Hartenstein
  • *Gödecke Forschungsinstitut, Mooswaldallee 1-9, D-7800 Freiburg, Federal Republic of Germany
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Publication Date:
20 August 2002 (online)

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Reaction of 2,5-dimethoxybenzaldehyde with tosylmethyl isocyanide in tetrahydrofuran in the presence of potassium tert-butoxide affords N-[2-(2,5-dimethoxyphenyl)-1-tosylethenyl]formamide with assumed E-stereochemistry. Reductive detosylation of this compound with sodium borohydride in dimethylformamide and O-demethylation of the resultant (Z)- N-[2-(2,5-dimethoxyphenyl)ethenyl]formamide with boron tribromide in dichloromethane yields cis-erbstatin whereas equilibration of (Z)- N-[2-(2,5-dimethoxyphenyl)ethenyl]formamide by irradiation in toluene in the presence of iodine, isolation of the E-isomer from the Z/E mixture thus formed, and O-demethylation with boron tribromide in dichloromethane yields (trans-)erbstatin.