Our main interest is to develop novel, one-pot synthesis procedures to access diverse sets of complex small molecules. We believe that using e.g. enzymes, less toxic and more common non-stoichiometric reagents and catalysts, and focus on atom-, step- and energy efficient one-pot processes provide great opportunities for innovative synthetic method development. The ‘ideal synthesis’ addresses high substituent, scaffold and stereo diversity and affords the desired products from readily available starting materials in a limited number of reaction steps. The synthetic approaches should proceed in good overall yield and selectivity and should maximize the incorporation of all materials used in the process into the final product. We apply these one-pot processes to access various APIs and complex natural products to show-case the power of our methodologies for sustainable, ‘green’ manufacturing processes.
The SyBOrCh group, on average 15 researchers, is headed by Prof. Romano Orru and Dr. Eelco Ruijter. They closely work together and share state-of-the-art laboratories and facilities including high-end equipment.
Research Highlights
Cascade Cyclizations
Braun, J.; Ariëns, M.I.; Matsuo, B.T.; de Vries, S.; van Wordragen, E.D.H.; Ellenbroek, B.D.; Vande Velde, C.M.L.; Orru, R.V.A; Ruijter, E. “Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji–Trost Cascade Cyclization” Org. Lett. 2018, 20, 6611-6615.
Iodospirocyclization of Tryptamine-Derived Isocyanides
Saya, J.M.; Roose, T.R.; Peek, J.J.; Weijers, B.; de Waal, T.S.J.; VandeVelde, C.M.L.; Orru, R.V.A.; Ruijter, E. “Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine” Angew. Chem. Int. Ed. 2018, 57, 15232-15236.
Universal Convertible Isocyanide for Multicomponent Chemistry
van der Heijden, G.; Jong, J.A.W.; Ruijter, E.; Orru R.V.A. “2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for Multicomponent Chemistry” Org. Lett. 2016, 18, 984-987.
Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction
de Graaff, C.; Bensch, L.; Boersma, S.J.; Cioc, R.C.; van Lint, M.J.; Janssen, E.; Turner, N.J.; Orru, R.V.A.; Ruijter, E. “Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction” Angew. Chem. Int. Ed. 2015, 54, 14133-14136.
Efficient Catalytic Access to Privileged Heterocycles: Palladium-catalyzed Isocyanide Insertion
Vlaar, T.; Cioc, R.C.; Mampuys, P.; Maes, B.U.W.; Orru, R.V.A.; Ruijter, E. “Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium-Catalyzed Aerobic Oxidative Isocyanide Insertion” Angew. Chem. Int. Ed. 2012, 51, 13058-13061.
Biocatalysis & MCRs: Synthesis of the Hepatitis C Drug Telaprevir
