Isolation, Chiral-Phase Resolution, and Determination of the Absolute Configurations of a Complete Series of Stereoisomers of a Rearranged Acetophenone with Three Stereocenters

A synthesis-inspired chemical investigation of the leaves of Melicope ptelefolia led to the isolation of evodialones A–D (1–4), four rearranged acetophenone stereoisomers possessing a prenylated acylcyclopentenone skeleton with three stereogenic carbons. Evodialones C and D (3 and 4) are new minor constituents. The chiral-phase HPLC resolution gave (+)-1–4 and (−)-1–4, eight enantiomers forming a complete stereoisomer library. Their absolute...