Synthetic studies on Stemona alkaloids. Construction of the sessilifoliamides B and C and 1,12-secostenine skeleton
Alonso-Fernández, Javier (Universitat Autònoma de Barcelona. Departament de Química)
Benaiges Miñarro, Cristina (Universitat Autònoma de Barcelona. Departament de Química)
Casas Arce, Eva (Universitat Autònoma de Barcelona. Departament de Química)
Alibes, Ramón (Universitat Autònoma de Barcelona. Departament de Química)
Bayón, Joan Carles (Universitat Autònoma de Barcelona. Departament de Química)
Busqué Sánchez, Félix (Universitat Autònoma de Barcelona. Departament de Química)
Alvarez-Larena, Angel (Universitat Autònoma de Barcelona. Servei de Cristal·lografia)
Figueredo Galimany, Marta (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2016
Abstract:	An original synthetic approach to the Stemona alkaloids stenine and sessilifoliamides B and C has been explored. The strategy relies on the early construction of the pyrroloazepine core (rings A and B) and latter addition of the furanone (ring D) and ethyl chain at C-10, which are the common structural features of the three alkaloids. The formation of the azabicyclic nucleus through an intramolecular Morita-Baylis-Hillman reaction of a properly substituted pyrrolidone has been extensively investigated by modifications on the substrate and all the parameters involved in the process and an efficient protocol in terms of yield and stereoselectivity has been developed. Despite many alternative tactics were explored, insurmountable difficulties found in the last synthetic steps have frustrated the completion of the syntheses. However, along the way, a plethora of new compounds was prepared, some of them containing the full skeleton of the targeted alkaloids, which can be useful for future synthetic applications.
Grants:	Ministerio de Ciencia e Innovación CTQ2010-15380 Ministerio de Economía y Competitividad CTQ2013-41161-R
Rights:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Pyrroloazepine ; Sessilifoliamides B and C ; Stemona alkaloids ; Stenine ; Stereoselective synthesis
Published in:	Tetrahedron, Vol. 72, Issue 24 (June 2016) , p. 3500-3524, ISSN 1464-5416

DOI: 10.1016/j.tet.2016.04.077

Postprint 29 p, 1.1 MB

The record appears in these collections:
Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Synthesis of Bioactive Organic Compounds and Functional Materials (SynOrgFUN)
Articles > Research articles
Articles > Published articles