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Synthesis 1990; 1990(7): 568-569
DOI: 10.1055/s-1990-26941
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A Short Stereoselective Synthesis of Erbstatin

J. Stoelwinder* , A. M. van Leusen
  • *Department of Organic Chemistry, Groningen University, Nijenborgh 16, NL-9747 AG Groningen, The Netherlands
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Publikationsdatum:
17. September 2002 (online)

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Reaction of diethyl (isocyanomethyl)phosphonate (2) with 2,5-dimethoxybenzaldehyde (1) in tetrahydrofuran in the presence of butyllithium affords 2-(2,5-dimethoxyphenyl) ethenyl isocyanide (3) with E-stereochemistry. Addition of hydrochloric acid at the isocyano carbon and hydrolysis of this adduct 4 yields (E)-O,O-dimethylerbstatin (5).