The First Synthesis of Sessiline

Viktor Ilkei^1*, Kornél Faragó¹, Zsuzsanna Sánta², Miklós Dékány², László Hazai¹, Csaba Szántay Jr.², Csaba Szántay¹, György Kalaus¹

¹Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary.
²Gedeon Richter Plc, Budapest, Hungary.

DOI: 10.4236/ijoc.2014.45033                

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.

Keywords

Sessiline, Acylaminocarbinol, Iminium Ion, Alkaloid Synthesis

Conflicts of Interest

The authors declare no conflicts of interest.

References

[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. http://dx.doi.org/10.1055/s-2002-34925
[2]	Hubert, J.C., Wijnberg, J.B.P.A. and Speckamp, W.N. (1975) NaBH4 Reduction of Cyclic Imides. Tetrahedron, 31, 1437-1441. http://dx.doi.org/10.1016/0040-4020(75)87076-1
[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. http://dx.doi.org/10.1080/00304947909355413
[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. http://dx.doi.org/10.3390/12030634
[6]	Schinzer, D., Bourguet, E., Ducki, S. (2004) Synthesis of Furano-Epothilone D. Chemistry—A European Journal, 10, 3217-3224. http://dx.doi.org/10.1002/chem.200400125
[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. http://dx.doi.org/10.1016/0223-5234(91)90101-R
[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. http://dx.doi.org/10.1016/0223-5234(91)90102-S