Natural products as a source of inspiration

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