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.

Share and Cite:

Ilkei, V. , Faragó, K. , Sánta, Z. , Dékány, M. , Hazai, L. , Szántay Jr., C. , Szántay, C. and Kalaus, G. (2014) The First Synthesis of Sessiline. International Journal of Organic Chemistry, 4, 309-313. doi: 10.4236/ijoc.2014.45033.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Lee, S., Ji, J., Shin, K.H. and Kim, B.-K. (2002) Sessiline, A New Nitrogenous Compound from the Fruits of Acanthopanax sessiliflorus. Planta Medica, 68, 939-941.
[2] Hubert, J.C., Wijnberg, J.B.P.A. and Speckamp, W.N. (1975) NaBH4 Reduction of Cyclic Imides. Tetrahedron, 31, 1437-1441.
[3] Cue Jr., B.W. and Chamberlain, N. (1979) An Improved Method for the Preparation of 5-Hydroxy-2-Pyrrolidone. Organic Preparations and Procedures International, 11, 285 286.
[4] Renvall, I. and Mattila, T. (1977) Esterification of Furfuryl Alcohol and Its Derivatives. US Patent No. 4008256.
[5] Mehner, A., Montero, A.L., Martinez, R. and Spange, S. (2007) Synthesis of 5-Acetoxymethyl- and 5-Hydroxymethyl- 2-Vinylfuran. Molecules, 12, 634-640.
[6] Schinzer, D., Bourguet, E., Ducki, S. (2004) Synthesis of Furano-Epothilone D. Chemistry—A European Journal, 10, 3217-3224.
[7] Toja, E., Gorini, C., Zirotti, C., Barzaghi, F. and Galliani, G. (1991) Amnesia-Reversal Activity of a Series of 5-Alkoxy-1-Arylsulfonyl-2-Pyrrolidinones. European Journal of Medicinal Chemistry, 26, 403-413.
[8] Toja, E., Gorini, C., Zirotti, C., Barzaghi, F. and Galliani, G. (1991) Amnesia-Reversal Activity of a Series of 5-Alkoxy-1-Arylcarbonyl-2-Pyrrolidinones and 5-Alkoxy-1-Arylmethyl-2-Pyrrolidinones. European Journal of Medicinal Chemistry, 26, 415-422.

Copyright © 2023 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.