Representative Publications
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Chemoselective AcylationWe develop new acylating reagents and activation modes that allow for broadly chemoselective acylation of polyfunctional molecules. Our ultimate goal is to allow for chemoselective acylation of any reactive site—regardless of inherent nucleophilicity—in a polyfunctional molecule without the need for protecting groups.
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- Dual Brønsted Acid/Nucleophilic Activation of Carbonylimidazole Derivatives. Heller, S. T.; Fu, T. T., Sarpong, R. Organic Letters, 2012, 14, 1970-1973.
- Chemoselective N-Acylation of Indoles and Oxazolidinones with Carbonylazoles. Heller, S. T.; Schultz, E. E.; Sarpong, R. Angewandte Chemie International Edition, 2012, 51, 8304-8308.
Heterocycle SynthesisWe employ our expertise in transition-metal catalysis and carbanion-mediated chemistries to streamline and expand the scope of the synthesis of complex nitrogen-containing ring systems. We also aim to develop novel cycloaddition strategies for the facile preparation of nitrogen heterocycles that are inaccessible by traditional techniques.
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Representative Publications
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- Rapid Access to Pyrazolo[3,4-c]pyridines via Alkyne Annulation: Limitations of Steric Control in Nickel-Catalyzed Alkyne Insertions. Heller, S. T.; Natarajan, S. R. Organic Letters, 2007, 9, 4947–4950.
- 1,3-Diketones from Acid Chlorides and Ketones: A Rapid and General One-Pot Synthesis of Pyrazoles. Heller, S. T.; Natarajan, S. R. Organic Letters 2006, 8, 2675-2678.
Representative Publications
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Natural Product SynthesisWe undertake the synthesis of complex bioactive natural products, with particular focus on cytotoxic alkaloids that reverse or combat multiple drug resistance in cancer cells. The goals of this program are threefold: (1) to supply collaborators with sufficient material to study mechanisms of action of these rare compounds, (2) to provide a proving ground for our synthetic expertise, and (3) provide inspiration for the development of new reactions and reagents.
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- Protic Solvent Mediated Cycloisomerization of Quinoline and Isoquinoline Propargylic Carbinols: Syntheses of (±)-3- Demethoxyerythratidinone and (±)-Cocculidine. Heller, S. T.; Kiho, T.; Narayan, A. R. H.; Sarpong, R. Angewandte Chemie International Edition, 2013, 52, 11129.