A Synthesis of Seco-mesembrane Alkaloids, (±)-Joubertiamine, (±)-Joubertinamine, and (±)-Epijoubertinamine

Abstract

A synthesis of seco-mesembrane alkaloids, (±)-joubertiamine (4), (±)-joubertinamine (5), and (±)-epijoubertinamine (6), was accomplished starting with 2-allyl-2-aryl-5, 5-ethylenedioxycyclohexanones (10 and 3), which are readily available by allylation of 2-aryl-5, 5-ethylenedioxycyclohexanones (9 and 16) with allyl bromide and 50% aqueous sodium hydroxide in the presence of 18-crown-6.