Download PDF
Synthesis 1988; 1988(12): 970-972
DOI: 10.1055/s-1988-27770
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >