Synthesis of erbstatin, a naturally occurring inhibitor of tyrosine-specific protein kinase

WK Anderson, TT Dabrah…

Index: Anderson, Wayne K.; Dabrah, Thomas T.; Houston, D. Michael Journal of Organic Chemistry, 1987 ,  vol. 52,  # 13  p. 2945 - 2947

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Citation Number: 16

Abstract

Conjugate addition of thiopheno15 to 3 (DMAP, THF, reflux) gave the thioether 4 in quantitative yield. Conversion of 4 to 5 was accomplished by lithium aluminum hydride (LiA1H4) reduction6 of the nitro group in an ether/THF solvent mixture under reflux conditions, the re-sulting primary amine (76%) was N-formylated with acetic formic anhydride (AFA)'in THF at-15 OC to give crys-talline (ethyl acetate-hexane) 5 in 91% yield. ...