Research ArticleOpen AccessGoogle Scholar indexed
The First Synthesis of Sessiline
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Gedeon Richter Plc, Budapest, Hungary
Gedeon Richter Plc, Budapest, Hungary
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Gedeon Richter Plc, Budapest, Hungary
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
- 1 Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
- 2 Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
- 3 Gedeon Richter Plc, Budapest, Hungary
- 4 Gedeon Richter Plc, Budapest, Hungary
- 5 Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
- 6 Gedeon Richter Plc, Budapest, Hungary
- 7 Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
- 8 Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
International Journal of Organic Chemistry·Volume 04 (2014)·Pages 309–313·Published 26 December 2014·DOI10.4236/ijoc.2014.45033
Copy link · social · email
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.
KeywordsSessilineAcylaminocarbinolIminium IonAlkaloid Synthesis
- 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
- 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
- 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
- Renvall, I. and Mattila, T. (1977) Esterification of Furfuryl Alcohol and Its Derivatives. US Patent No. 4008256.
- 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
- 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
- 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
- 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