Total synthesis of lycoperdic acid and stereoisomers (part 1): Double asymmetric hydrogenation of a racemic enamide

Design, synthesis, and double asymmetric hydrogenation of a racemic enamide are reported toward stereodivergent synthesis of lycoperdic acid and its isomers. The hydrogenation outcome (yield, ee) was used to identify matched and mismatched products, the information is important to clarify the reaction mechanism. It is also proposed that if the reaction mechanism is known, structure of the products would be identified without spectroscopic analyses from the matched/mismatched analysis.