Biomimetic synthesis of nazlinin and nitrarine

Abstract

The presence of rather complicated alkaloids in Nitraria species as racemates suggests a non-enzymic biosynthesis of the skeletons, which implies that these reactions should be reproducible in the lab. In the case of Nitramine and Nitraramine the total synthesis was approached starting from highly symmetric glutarimide derivatives. Insight in the biosynthesis of Nitraria alkaloids led to a revision of the structure of Nazlinin. In the case of Nitrarine it was shown that spontaneous cyclizations to the racemic alkaloid skeleton occurred once the reactive precursor, containing an imine and an enamine functionality was treated with acid. © 1994 IUPAC