A Simple Synthesis of Erbstatin and Its cis -Isomer
1988; Thieme Medical Publishers (Germany); Volume: 1988; Issue: 12 Linguagem: Inglês
10.1055/s-1988-27770
ISSN1437-210X
AutoresJ. KLEINSCHROTH, Johannes Hartenstein,
Tópico(s)Synthesis and Reactions of Organic Compounds
ResumoReaction 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.
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