Catalytic Approaches to Simplifying Synthesis

Seminar | October 10 | 11 a.m.-12 p.m. | 120 Latimer Hall

 Prof. Darren Dixon, Department of Chemistry, University of Oxford

 College of Chemistry

Catalysts that provide new reactivity and stereocontrol in efficient bond-forming reactions, are essential tools for converting low cost starting materials into high value, structurally complex, stereochemically defined product materials. In this presentation, new families of metal-free and metal-rich cooperative catalysts and their use in highly enantioselective C-C bond forming reactions and other relevant transformations, will be described.

Their strategic application to the discovery of new one-pot reaction cascade processes to generate novel, stereochemically defined scaffolds and architectures useful for library and target synthesis will also be discussed. Further application of selected methodologies as pivotal carbon-carbon bond forming steps in the total synthesis of a range of manzamine, aspidosperma, iboga, strychnos and daphniphyllum alkaloids will then be discussed. These syntheses serve to illustrate how complex molecular targets can be rapidly accessed when combinations of catalyst-controlled reactions, one-pot multistep procedures and powerful route-shortening cascades are designed into the overall synthetic sequence.




References:
[1] F. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon, J. Am. Chem. Soc. 2011, 133, 1710.
[2] M. Yu, C. Wang, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Nature, 2011, 479, 88.
[3] P. Jakubec, A. Hawkins, W. Felzmann, D. J. Dixon, J. Am. Chem. Soc. 2012, 134, 17482.
[4] M. G. Núñez, A. J. M. Farley, D. J. Dixon, J. Am. Chem. Soc. 2013 135, 16348.
[5] I. Ortín, D. J. Dixon, Angew. Chem. Int. Ed. 2014, 53, 3462.
[6] A. D. Gammack Yamagata, S. Datta, K. E. Jackson, L. Stegbauer, R. S. Paton, D. J. Dixon, Angew. Chem. Int. Ed. 2015, 54, 4899.
[7] R. De La Campa, I. Ortín, D. J. Dixon, Angew. Chem. Int. Ed. 2015, 54, 4895.
[8] A. J. M. Farley, C. Sandford, D. J. Dixon, J. Am. Chem. Soc. 2015, 137, 15992.
[9] J. Yang, A. J. M. Farley, D. J. Dixon, Chemical Science, 2017, 8, 606.
[10] P. W. Tan, J. Seayad, D. J. Dixon, Angew. Chem. Int. Ed. 2016, 55, 13436.

 Light refreshments will be served at 10:50 at The Coffee Lab

 seminarcoordinator-cchem@berkeley.edu, 510-643-0572