TITLE:
The First Synthesis of Sessiline
AUTHORS:
Viktor Ilkei, Kornél Faragó, Zsuzsanna Sánta, Miklós Dékány, László Hazai, Csaba Szántay Jr., Csaba Szántay, György Kalaus
KEYWORDS:
Sessiline, Acylaminocarbinol, Iminium Ion, Alkaloid Synthesis
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.4 No.5,
December
26,
2014
ABSTRACT: 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.