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Accueil du site > LPCNO > Séminaires > 2015 > Designing radical cyclization cascades : New methods for target synthesis

Designing radical cyclization cascades : New methods for target synthesis

Séminaire conjoint LCC/LPCNO

Date : 30/01/2015 à 11:00

Titre : Designing radical cyclization cascades : New methods for target synthesis.

Intervenant : David Procter

Provenance : School of Chemistry, University of Manchester. Manchester. M13 9PL, UK

Salle : Auditorium Fernand Gallais au LCC

Résumé : We will describe the development of novel radical cascade processes enabled by a toolbox of new lanthanide(II) electron transfer reagents.[1] New functional group reductions[2] and reductive cyclizations[3] mediated by activated lanthanide (II) complexes will be introduced. For example, we have recently reported that the treatment of unsaturated esters with SmI2–H2O triggers radical cyclization cascades to form complex products in high yield with good diastereocontrol.[3] The presentation will conclude with the application of a Sm(II)-mediated cascade cyclization in the total synthesis of the antibacterial natural product (+)-pleuromutilin.[4]

[1] For recent reviews, see : (a) Szostak, M. ; Fazakerley, N. J. ; Parmar, D. ; Procter, D. J. Chem. Rev. 2014, in press. (b) Szostak, M. ; Spain, M. ; Procter, D. J. Chem. Soc. Rev. 2013, 42, 9155. (c) Szostak, M. ; Procter, D. J. Angew. Chem. Int. Ed. 2012, 51, 9238.

[2] For selected recent examples, see : (a) Guazzelli, G. ; De Grazia, S. ; Collins, K. D. ; Matsubara, H. ; Spain, M. ; Procter, D. J. J. Am. Chem. Soc. 2009, 131, 7214. (b) Szostak, M. ; Spain, M. ; Procter, D. J. Angew. Chem. Int. Ed. 2013, 52, 7237. (c) Szostak, M. ; Spain, M. ; Choquette, K. A. ; Flowers, II, R. A. ; Procter, D. J. J. Am. Chem. Soc. 2013, 135, 15702. (d) Szostak, M. ; Spain, M. ; Eberhart, A. J. ; Procter, D. J. J. Am. Chem. Soc. 2014, 136, 2268.

[3] For selected recent examples, see : (a) Parmar, D. ; Price, K. ; Spain, M. ; Matsubara, H. ; Bradley, P. A. ; Procter, D. J. J. Am. Chem. Soc. 2011, 133, 2418. (b) Parmar, D. ; Matsubara, H. ; Price, K. ; Spain, M. ; Procter, D. J. J. Am. Chem. Soc. 2012, 134, 12751. (c) Szostak, M. ; Sautier, B. ; Behlendorf, M. ; Procter, D. J. Angew. Chem. Int. Ed. 2013, 52, 12559.

[4] (a) Fazakerley, N. J. ; Helm, M. D. ; Procter, D. J. Chem. -Eur. J. 2013, 19, 6718. (b) Helm, M. D. ; Da Silva, M. ; Sucunza, D. ; Findley, T. J. K. ; Procter, D. J. Angew. Chem. Int. Ed. 2009, 48, 9315.