Total synthesis of (–)-solavetivone using enantioselective copper-catalysed conjugate addition of Me3Al to a cyclohexa-2,5-dienone intermediate

Abstract

By applying a new enantioselective Cu-catalysed conjugate addition of Me₃Al, (–)-solavetivone 1 is synthesized stereoselectively from cyclohexa-2,5-dienone 4, prepared from a chiral compound 6 using a regioselective Hg^II-mediated cyclopropyl ring-opening, subsequent Pd^II-mediated spiroannulation of 7, and a stereoselective Pd⁰-catalysed hydrogenation of an allylic formate 5 as key reactions.