Enantioselective Cooperative Catalysis and Complexity Building Reaction Cascades in Library and Natural Product Synthesis

Feb13Wed

Enantioselective Cooperative Catalysis and Complexity Building Reaction Cascades in Library and Natural Product Synthesis

Wed, 13/02/2013 - 16:00 to 17:00

Location:

Speaker: 
Prof. Darren Dixon
Affiliation: 
University of Oxford
Synopsis: 

Enantiomerically pure compounds with the capacity to activate simultaneously electrophilic substrates and pro-nucleophilic reagents towards one another, offer numerous opportunities for the discovery of powerful new catalytic asymmetric carbon-carbon and carbon-heteroatom bond forming reactions. In this presentation, new families of bifunctional catalysts derived from cinchona alkaloids and their use in highly enantioselective Michael addition reactions, Mannich reactions, aldol reactions and alkylation reaction as well as other synthetically relevant transformations, will be described.

The application of selected methodologies as pivotal carbon-carbon bond forming steps in the total synthesis of Manzamine alkaloids (–)-Nakadomarin A and Manzamine A will then be discussed. These syntheses serve to illustrate how significant quantities of natural product 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: (a) J. Ye, D. J. Dixon, P. S. Hynes, Chem. Comm. 2005, 4481. (b) A. L. Tillman, J. Ye, D. J. Dixon, Chem. Comm. 2006, 1191. (c) P. Jakubec, D. Cockfield and D. J. Dixon J. Am. Chem. Soc. 2009, 131, 16632. (d) F. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon, J. Am. Chem. Soc. 2011, 133,1710. (e) M. Yu, C. Wang, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Nature 2011, 479, 88. (f) P. Jakubec, A. Hawkins, W. Felzmann and D. J. Dixon, J. Am. Chem. Soc. 2012, 134, 17482.

Biography: 

Darren J. Dixon is Professor of Chemistry at the University of Oxford. He obtained his first degree and D. Phil from the University of Oxford, where he worked with Professor Stephen G. Davies. In 1997 he moved to the University of Cambridge to undertake post-doctoral work with Professor Steven V. Ley CBE, FRS and in 2000 was appointed to the staff of the Department of Chemistry. In September 2004 he was appointed to a Senior Lectureship at The University of Manchester and in August 2007 was promoted to Reader. In October 2008 he moved to his current post at the University of Oxford where he also holds the Knowles-Williams Tutorial Fellowship in Organic Chemistry at Wadham College.

His research interests lie largely in the field of asymmetric synthesis where he has published widely on catalyst design and application, the design and development of synthetically powerful reaction cascades, the development of new synthetic methodologies and the total synthesis of complex natural products.

He has published 120 primary research papers and is the recipient of an EPSRC Leadership Fellowship. In 2010 was awarded the inaugural Royal Society of Chemistry’s ‘Catalysis in Organic Chemistry Award’, and ‘the 2010 AstraZeneca Research Award in Organic Chemistry’. He was awarded the Novartis Lectureship in Central Europe (2011) and the Kende Distinguished Lectureship, University of Rochester, USA (2013).

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