168111-92-0Relevant articles and documents
A simple synthesis of bannucine and 5′-epibannucine from (-)-vindoline
Ilkei, Viktor,Bana, Péter,Tóth, Flórián,Palló, Anna,Holczbauer, Tamás,Czugler, Mátyás,Sánta, Zsuzsanna,Dékány, Miklós,Szigetvári, áron,Hazai, László,Szántay, Csaba,Szántay, Csaba,Kalaus, Gy?rgy
, p. 9579 - 9586 (2015)
Bannucine is an Aspidosperma alkaloid isolated from the dried leaves of Catharanthus roseus. The molecule is a derivative of vindoline bearing a C10 substituent, a pattern common to the antineoplastic dimeric indole alkaloids of C. roseus. In bannucine, a 2-pyrrolidone moiety is attached at C5′ to the aromatic ring of the vindoline core at C10. In the present work we report the synthesis of bannucine and its 5′-epimer from natural (-)-vindoline using a cyclic N-acyliminium ion intermediate whose N-acylaminocarbinol precursor is synthesized by the partial reduction of succinimide. We also describe the separation and the structural analysis of the two epimers, using among others, single crystal X-ray diffraction methods, in order to clarify the orientation of the proton attached to the C5′ carbon. The in vitro antineoplastic activity of the pure epimers was also investigated, but none of the two substances showed significant activity on the examined tumour cell lines.
PSEUDOESTERS AND DERIVATIVES. XXII. SYNTHESIS OF 5-HYDROXY-3-PYRROLIN-2-ONES AND 5-HYDROXYPYRROLIDIN-2-ONES BY AMMONOLYSIS OF 5-METHOXYFURAN-2(5H)-ONES AND DERIVATIVES
Farina, Francisco,Martin, M. Victoria,Paredes, M. Carmen,Ortega, M. Carmen,Tito, Amelia
, p. 1733 - 1739 (2007/10/02)
The ammonolysis of 4-substituted 5-methoxyfuran-2(5H)-ones 4a-e under mild conditions affords the respective 5-hydroxy-3-pyrrolin-2-ones 5a-e.However, 4-dialkylamino derivatives 4f,g do not react with ammonia under the same conditions.Similar ammonolysis of furanone derivatives 7a,b, 10 and 13 yields the pyrrolidinones 8a,b and hexahydroisoindolones 11, and 14, respectively.The corresponding methoxylactams 6a-e, 9a-b and 12 are readily obtained by refluxing the hydroxylactams 5a-e, 8a,b and 11, respectively with acid-catalyzed methanol.