Abstract: Nature has evolved highly sophisticated machinery for organic synthesis, many of which resemble molecular assembly-line processes. So far chemists have been able to apply this type of approach in the synthesis of peptides and oligonucleotides but in these reactions, simple amide (C‒N) or phosphate (P‒O) bonds are created. It is much more difficult to make C‒C bonds but this is central to the discipline of organic synthesis. This difficulty is why organic synthesis is challenging and why robust, iterative or automated methodologies have not yet emerged.
In this talk Prof Aggarwal will describe the application of iterative homologation of boronic esters using chiral lithiated benzoate esters and chloromethyllithium to the highly efficient syntheses of several natural products. He will also show how the methodology can be used to determine the structure of natural products which have been incorrectly assigned.5
Secondary and tertiary boronic esters are versatile intermediates and can be transformed into alcohols, alkenes, and amines. Prof Aggarwal will show how this can be expanded to include new coupling reactions with a broad range of aromatics, and also new reactions that convert the boronic ester moiety into a host of other functional groups with full stereocontrol 5
In this talk Prof Aggarwal will describe the application of iterative homologation of boronic esters using chiral lithiated benzoate esters and chloromethyllithium to the highly efficient syntheses of several natural products. He will also show how the methodology can be used to determine the structure of natural products which have been incorrectly assigned.5
Secondary and tertiary boronic esters are versatile intermediates and can be transformed into alcohols, alkenes, and amines. Prof Aggarwal will show how this can be expanded to include new coupling reactions with a broad range of aromatics, and also new reactions that convert the boronic ester moiety into a host of other functional groups with full stereocontrol 5
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- S. Balieu, G. E. Hallett, M. Burns, T. Bootwicha, J. Studley, V. K. Aggarwal, J. Am. Chem. Soc. 2015, 137, 4398.
- M. Burns, S. Essafi, J. R. Bame, S. P. Bull, M. P. Webster, S. Balieu, J. W. Dale, C. P. Butts, J. N. Harvey, V. K. Aggarwal, Nature, 2014, 513, 183.
- J. Wu, P. Lorenzo, S. Zhong, M. Ali, C. P. Butts, E. L. Myers, V. K. Aggarwal, Nature, 2017, 547, 436.
- C. Sandford, V. K. Aggarwal Chem. Commun., 2017, 53, 5481.
