résumé (Format PDF) - ED 406 - Université Pierre et Marie CURIE

Journées Bibliographiques de l’EDCM
Coralie TUGNY
Synthetic approaches to angular triquinanes
Louis Fensterbank
Institut Parisien de Chimie Moléculaire (IPCM) - UMR 7201
4, Place Jussieu, 75252 Paris Cedex 05
louis.fensterbank@upmc.fr
Angular triquinane sesquiterpenes constitute an important class of natural products,
with both their structural and biological properties being attractive. Thus, there has been
significant interest in the construction of their highly condensed framework 1
for the
construction of which the strategies described in the literature are extremely various. 2 Most of
them are employing cycloaddition reactions, either metal-catalyzed or not, as they certainly
are among the most efficient reactions in producing increased molecular complexity. 3 Radical
chemistry offers the possibility of cascade reactions. In particular, tandem 5-exo-trig radical
cyclizations allow rapid access to the angular triquinane framework. 4
Electrocyclization
reactions are much less represented. One nonetheless constitutes a particularly impressive
scaffolding. 5
1 Pierre, M.-C., Tenaglia, A., Santelli, M. Tetrahedron 1998, 54, 14803-14810; Singh, V., Lahiri, S. Tetrahedron
Lett. 2003, 44, 4239-4242; Srikrishna, A., Gowri, V. Tetrahedron: Asymm. 2011, 22, 1553-1559; Seo, J., Fain,
H., Blanc, J.-B., Montgomery, J. J. Org. Chem. 1999, 64, 6060-6065; Gharpure, S.J., Niranjana, P., Porwal, S.K.
Org. Lett. 2012, 14, 5476-5479.
2 Mehta, G., Srikrishna, A. Chem. Rev. 1997, 97, 671-719.
3 Meyer, C., Marek, I., Normant, J.-F. Tetrahedron Lett. 1996, 37, 857-860; Renaud, J.-L., Aubert, C., Malacria,
M. Tetrahedron 1999, 55, 5113-5128; Rawal, V.H., Dufour, C. J. Am. Chem. Soc. 1994, 116, 2613-2614;
Veenstra, S.J., De Mesmaeker, A., Ernst, B. Tetrahedron Lett. 1988, 29, 2303-2306.
4 Curran, D.P., Sisko, J., Balog, A., Sonoda, N., Nagahara, K., Ryu, I. J. Chem. Soc., Perkin Trans 1 1998, 1591-
1593; Curran, D.P., Kuo, S.-C. Tetrahedron 1987, 43, 5653-5661; De Boeck, B., Harrington-Frost, N.M.,
Pattenden, G. Org. Biomol. Chem. 2005, 3, 340-347.
5 Paquette, L.A., Doyon, J. J. Org. Chem. 1997, 62, 1723-1729.