Cornali, B. M., Kimani, F. W., & Jewett, J. C. (2016). Cu-Click Compatible Triazabutadienes To Expand the Scope of Aryl Diazonium Ion Chemistry. Organic letters, 18(19), 4948-4950.
Triazabutadienes can be used to readily generate reactive aryl diazonium ions under mild, physiologically relevant conditions. These conditions are compatible with a range of functionalities that do not tolerate traditional aryl diazonium ion generation. To increase the utility of this aryl diazonium ion releasing chemistry an alkyne-containing triazabutadiene was synthesized. The copper-catalyzed azide-alkyne cycloaddition ("Cu-click") reaction was utilized to modify the alkyne-containing triazabutadiene and shown to be compatible with the nitrogen-rich triazabutadiene. One of the triazole products was tethered to a fluorophore, thus enabling the direct fluorescent labeling of a model protein.
Gálvez, E., Romea, P., Urpí, F., Jewett, J. C., & Rawal, V. H. (2009). Preparation of (S)-4-Isopropyl-N-propanoyl-1,3-thiazolidine-2-thione. Organic Syntheses, 86, 70-80.
Martinez-Ariza, G., Mehari, B. T., Pinho, L., Foley, C., Day, K., Jewett, J. C., & Hulme, C. (2017). Synthesis of fluorescent heterocycles via a Knoevenagel/[4+1]-cycloaddition cascade using acetyl cyanide. ORGANIC & BIOMOLECULAR CHEMISTRY, 15(29), 6076-6079.
Jewett, J. C., & Rawal, V. H. (2007). Total synthesis of pederin. Angewandte Chemie - International Edition, 46(34), 6502-6504.
PMID: 17645272;Abstract:
(Chemical Equation Presented) Blisteringly fast: The potent cytotoxic blistering agent pederin has been synthesized (see scheme). The synthesis is diastereoselective and concise (just 12 steps for the longest linear sequence), and features a formal hetero-Diels-Alder reaction of a hindered diene, a Mukaiyama-Michael reaction to set two additional stereocenters, and a Curtius rearrangement to stereospecifically introduce the aminal functionality. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
Jewett, J. C., & Bertozzi, C. R. (2010). Cu-free click cycloaddition reactions in chemical biology. Chemical Society Reviews, 39(4), 1272-1279.
PMID: 20349533;PMCID: PMC2865253;Abstract:
Bioorthogonal chemical reactions are paving the way for new innovations in biology. These reactions possess extreme selectivity and biocompatibility, such that their participating reagents can form covalent bonds within richly functionalized biological systems - in some cases, living organisms. This tutorial review will summarize the history of this emerging field, as well as recent progress in the development and application of bioorthogonal copper-free click cycloaddition reactions. © 2010 The Royal Society of Chemistry.