Stereoselectivity in the organoiron-mediated synthesis of (±)-mesembrine

The preparation and structural characterisation of a 1-aryl-substituted electrophilic η5-cyclohexadienyliron complex with the correct functionalisation as a ‘C12 building block’ for the synthesis of (±)-mesembrine establishes the accessibility of a flattened conformation to allow nucleophile addition ipso to the arene. The chirality relay in quaternary centre formation by nucleophile addition has been confirmed, and the product has been converted into the Sceletium alkaloid mesembrine.

A 1-aryl-substituted electrophilic η5-cyclohexa-dienyliron ‘C12 building block’ for the synthesis of (±)-mesembrine adopts a flattened conformation to allow nucleophile addition ipso to the arene.Figure optionsDownload as PowerPoint slide