Natural products as a source of inspiration
Transcription
Natural products as a source of inspiration
Natural products as a source of inspiration Jean-François Poisson Univ. Grenoble Alpes, DCM, F-38000 Grenoble, France CNRS, DCM, F-38000 Grenoble, France E-Mail : jean-franç[email protected] Lycorine-type alkaloids, extracted from the Amaryllidaceae family of plants, are structurally and biologically stimulating. Their biological activities1and low natural abundance, combined with the few available asymmetric syntheses2 and redundant mis-assignment of the structure of congeners 3 prompt synthetic chemists to investigate synthetic approaches to this challenging class of natural product. This lecture will focus on our recent progress to elaborate a flexible synthetic strategy for the synthesis of several congeners of the Lycorine family that required the development of novel reagent and methods.4 OH HO H O H O H H O H N O N H O Lycorine α-Lycorane H O O H O N Narcissidine 1 O OH H N γ-Lycorane O HO H HO HO O H HO OH H H O N Fortucine H O N Siculinine D. Lamoral-Theys, A. Andolfi, G. Van Goietsenoven, A. Cimmino, B. Le Calvé, N. Wauthoz, V. Mégalizzi, T. Gras, C. Bruyère, J. Dubois, V. Mathieu, A. Kornienko, R. Kiss, A. Evidente J. Med. Chem. 2009, 52, 6244. 2 Yamada, R.; Yamashita, M.; Sumiyoshi, T.; Nishimura, K.; Tomioka, K. Org. Lett. 2009, 11, 1631. 3 (a) Biechy, A.; Hachisu, S.; Quiclet-Sire, B.; Ricard, L.; Zard S. Z. Angew. Chem. Int. Ed. 2008, 47, 1436. (b) D. Liu, D.; Chen, J.; Ai, L.; Zhang, H.; Liu, J. Org. Lett. 2013, 15, 410. (c) Beaulieu, M-A.; Ottenwaelder, X.; Canesi S. Chem. Eur. J. 2014, 20, 7581. 4 Under publication 4 Under publication