The First Synthesis of Sessiline

Sessiline is an alkaloid which is recently isolated from the fruits of Acanthopanax sessiliflorus. The molecule contains two five-membered heterocyclic units joined together by an acylaminocarbinol-ether type bond. Here, we describe the first, simple synthesis of sessiline from 5-hydroxypyrrolidin-2-one and 5-hydroxymethylfurfural, which are prepared from succinimide and furfuryl alcohol, respectively. The coupling reaction takes place on moderate heating under neat conditions.