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

The preparation and structural characterisation of a 1-aryl-substituted electrophilic eta(5)-cyclohexadienyliron complex with the correct functionalisation as a 'C-12 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. (c) 2007 Elsevier Ltd. All rights reserved.