Structural Revision and Synthesis of Sinharine and Methylsinharine

Abstract

An unambiguous synthesis of the published structure for the natural product sinharine (1) showed that the assignment was incorrect. (E)-3-( Methylthio )-N-(2-phenylethyl) propenamide (4) was proposed as an alternative structure and this was confirmed by synthesis. Similarly the literature proposal for the structure of methylsinharine was reviewed and the natural product tentatively reassigned as (E)-N-methyl-3-( methylthio )-N-(2-phenylethyl) propenamide.