11:00 à 12:00
Conférencier invité
Non enregistré

Total Synthesis with Designed Hydrocarbons

Michael Sherburn
11:00 à 12:00
Amphithéâtre Maurice Halbwachs, Site Marcelin Berthelot
En libre accès, dans la limite des places disponibles
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Image générée à l'aide d'une I.A. - © Michael Sherburn.

Michael Sherburn est invité par l'assemblée du Collège de France sur proposition du professeur Louis Fensterbank.

Résumé

We design, synthesise, and study simple unsaturated hydrocarbons, seeking to understand what makes them tick and how they can be exploited in the synthesis of complex natural products. This programme deliberately bridges two disciplines that rarely meet: fundamental hydrocarbon chemistry and total synthesis.

Our strategy is built around sequences of cross-coupling and pericyclic reactions that generate large amounts of molecular complexity in very few operations. The prevailing view is that short syntheses are achieved by starting with complex materials and adding relatively little new complexity. We pursue the opposite strategy. Beginning with exceptionally simple molecules, we generate complexity rapidly and nevertheless arrive at natural product targets in surprisingly few steps.

The talk will describe the conceptual framework behind this work, several methodological developments arising from it, and their application in total synthesis. It will conclude with some speculation on how these ideas might evolve as increasingly complex molecules are assembled from ever simpler starting materials. 

Illustration présentant quatre structures chimiques de composés organiques naturels, représentées sous forme de formules développées avec cycles carbonés, groupements hydroxyle, méthyle et carbonyle

Références

Short review: M. S. Sherburn Acc. Chem. Res. 2015, 48, 1961–1970; recent papers: J. J. Lee, N. L. Magann, M. G. Gardiner, and M. S. Sherburn Angew. Chem. Int. Ed. 2026, e16522; Z. Pei, N. L. Magann, M. J. Sowden, R. L. Murphy, M. G. Gardiner, M. S. Sherburn, M. L. Coote, J. Am. Chem. Soc. 2023145, 16037–16044, N. L. Magann, E. Westley, M. J. Sowden, M. G. Gardiner, M. S. Sherburn J. Am. Chem. Soc. 2022, 144, 19695–19699: Y.-M. Fan, M. J. Sowden, N. L. Magann, E. J. Lindeboom, M. G. Gardiner, M. S. Sherburn, J. Am. Chem. Soc. 2022, 144, 20090–20098; Y.-M. Fan, L.-J. Yu, M. L. Coote, M. S. Sherburn Angew. Chem. Int. Ed., 2022, 61, e202204872; J.-Y. Wang, M. Blyth, M. S. Sherburn, M. L. Coote, J. Am. Chem. Soc, 2022, 144, 1023-1033; E. Westley, M. J. Sowden, N. L. Magann, K. L. Horvath, K. P. E. Connor, M. S. Sherburn, J. Am. Chem. Soc, 2022, 144, 977-986.