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Séminaire Chimie ED459

Exploring chemical reactivities to maximize structural diversity : application to natural product synthesis

Dr. Stellios Arseniyadis (Laboratoire de Chimie Organique, UMR 7084 CNRS, ESPCI ParisTech)

publié le

Le Jeudi 10 Octobre 2013 à 13h45
UM2, salle de cours SC-16.01

For the past several years, the group has focused on the development of useful synthetic tools and executing creative and efficient routes towards biologically active natural products. In this context, we recently applied the palladium-catalyzed decarboxylative allylic alkylation reaction to a new class of substrates, namely allyl dienol carbonates. This method allowed a particularly straightforward access to butenolides bearing an α-quaternary stereogenic center in both high yields and high enantioselectivities and was eventually used in the total synthesis of (−)-nephrosteranic acid and (−)-roccellaric acid.[1] This palladium-catalyzed decarboxylative allylic alkylation reaction was also used in a one-pot four-step sequence to access polysubstituted furans.[2]

Fig 1

Figure 1 (click to enlarge)

We have also been interested in the development of useful synthetic tools for the preparation of thiazolcontaining natural products as this motif is present in a number of compounds exhibiting interesting biological activities. Surprisingly, while the olefin cross-metathesis and the enantioselective organocatalytic conjugate reduction of α,β-unsaturated aldehydes had been wildly used on a number of substrates, their were no examples involving thiazol-containing substrates. We therefore adapted these two key transformations to such coumpounds[3,4] and applied the methods to the total synthesis of various natural products including melithiazole A, C, G and H, cystothiazole A and F and more recently (+)-myxothiazole Z.[5]

Fig 2

Figure 2 (click to enlarge)

References

1. J. Fournier, O. Lozano, C. Menozzi, S. Arseniyadis, J. Cossy, Angew. Chem. Int. Ed. 2013, 52, 1257-1261.
2. J. Fournier, S. Arseniyadis, J. Cossy, Angew. Chem. Int. Ed. 2012, 51, 7562-7566.
3. J. Dash, S. Arseniyadis, J. Cossy, Adv. Synth. Cat. 2007, 349, 152-156.
4. T. J. Hoffman, J. Dash, J. H. Rigby, S. Arseniyadis, J. Cossy, Org. Lett. 2009, 11, 2756-2759.
5. a) J. Gebauer, S. Arseniyadis, J. Cossy, Org. Lett. 2007, 9, 3425-3427 ; b) J. Gebauer, S. Arseniyadis, J. Cossy, Eur. J. Org. Chem. 2008, 2701-2704 ; c) A. Colon, T. J. Hoffman, J. Gebauer, J. Dash, J. H. Rigby, S. Arseniyadis, J. Cossy, Chem. Commun. 2012, 48, 10508-10510.

Contact local IBMM : Dr. Michael Smietana (DACAN)

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