Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

Scholarly Works

• Fuse, Y.; Ookubo, S.; Yoshimura, T.; Matsuo, J. Synthesis of 13–16‐Membered Cyclotetrapeptide Mimics by Ugi Reactions with Diacids and Diisonitriles. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202300939
• González, R.; Murillo-López, J.; Rabanal-León, W.; Prent-Peñaloza, L.; Concepción, O.; Olivares, P.; Duarte, Y.; de la Torre, A. F.; Gutiérrez, M.; Caballero, J. Multicomponent synthesis and photophysical study of novel α,β-unsaturated carbonyl depsipeptides and peptoids. Frontiers in chemistry 2023, 11, 1245941. doi:10.3389/fchem.2023.1245941
• Rosalba, T. P. F.; Matos, G. D. R.; Salvador, C. E. M.; Andrade, C. K. Z. Rational Design and Multicomponent Synthesis of Lipid-Peptoid Nanocomposites towards a Customized Drug Delivery System Assembly. Molecules (Basel, Switzerland) 2023, 28, 5725. doi:10.3390/molecules28155725
• Nikoofar, K.; Yielzoleh, F. M. High-component Reactions (HCRs): An Overview of MCRs Containing Seven or More Components as Versatile Tools in Organic Synthesis. Current organic synthesis 2022, 19, 115–147. doi:10.2174/1570179418666210910111208
• Zhang, W. doi:10.1002/9783527832439.ch5
• Andrade, C. K. Z.; Salvador, C. E. M.; Rosalba, T. P. F.; Corrêa, L. Z. A.; Martinho, L. A.; Sousa, Y. R. doi:10.1002/9783527832439.ch11
• Rosalba, T. P. F.; Kas, S. S. A.; Sampaio, A. B. S.; Salvador, C. E. M.; Andrade, C. K. Z. The Ugly Duckling Metamorphosis: The Ammonia/Formaldehyde Couple Made Possible in Ugi Reactions. European Journal of Organic Chemistry 2021, 2021, 2831–2842. doi:10.1002/ejoc.202001671
• Graebin, C. S.; Ribeiro, F. V.; Rogério, K. R.; Kümmerle, A. E. Multicomponent Reactions for the Synthesis of Bioactive Compounds: A Review. Current organic synthesis 2019, 16, 855–899. doi:10.2174/1570179416666190718153703
• Salvador, C. E. M.; Andrade, C. K. Z. A mild, fast and scalable synthesis of substituted α-acyloxy ketones via multicomponent reaction using a continuous flow approach. Frontiers in chemistry 2019, 7, 531. doi:10.3389/fchem.2019.00531
• Zhi, S.; Ma, X.; Zhang, W. Consecutive multicomponent reactions for the synthesis of complex molecules. Organic & biomolecular chemistry 2019, 17, 7632–7650. doi:10.1039/c9ob00772e
• Tao, Y.; Wang, Z.; Tao, Y. Polypeptoids synthesis based on Ugi reaction: Advances and perspectives. Biopolymers 2019, 110, e23288. doi:10.1002/bip.23288
• de Fátima S. Barreto, A.; Andrade, C. K. Z. Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions. Beilstein journal of organic chemistry 2019, 15, 906–930. doi:10.3762/bjoc.15.88
• de Fátima S. Barreto, A.; Andrade, C. K. Z. Microwave-mediated synthesis of a cyclic heptapeptoid through consecutive Ugi reactions. Tetrahedron 2018, 74, 6861–6865. doi:10.1016/j.tet.2018.10.018
• de Fátima S. Barreto, A.; dos Santos, V. A.; Andrade, C. K. Z. Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Beilstein journal of organic chemistry 2017, 13, 2596–2602. doi:10.3762/bjoc.13.256
• Wessjohann, L. A.; Filho, R. A. W. N.; Puentes, A. R.; Morejón, M. C. doi:10.1002/9781119092599.ch14
• Lee, Y.; Phat, C.; Hong, S. C. Structural diversity of marine cyclic peptides and their molecular mechanisms for anticancer, antibacterial, antifungal, and other clinical applications. Peptides 2017, 95, 94–105. doi:10.1016/j.peptides.2017.06.002
• Morejón, M. C.; Laub, A.; Kaluđerović, G. N.; Puentes, A. R.; Hmedat, A.; Otero-González, A. J.; Rivera, D. G.; Wessjohann, L. A. A multicomponent macrocyclization strategy to natural product-like cyclic lipopeptides: synthesis and anticancer evaluation of surfactin and mycosubtilin analogues. Organic & biomolecular chemistry 2017, 15, 3628–3637. doi:10.1039/c7ob00459a
• de Fátima S. Barreto, A.; dos Santos, V. A.; Andrade, C. K. Z. Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions. Beilstein journal of organic chemistry 2016, 12, 2865–2872. doi:10.3762/bjoc.12.285
• Abdel-Raheem, E. M. M.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Dömling, A. Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure. The Journal of organic chemistry 2016, 81, 8789–8795. doi:10.1021/acs.joc.6b01430
• Wessjohann, L. A.; Morejón, M. C.; Ojeda, G. M.; Rhoden, C. R. B.; Rivera, D. G. Applications of Convertible Isonitriles in the Ligation and Macrocyclization of Multicomponent Reaction-Derived Peptides and Depsipeptides. The Journal of organic chemistry 2016, 81, 6535–6545. doi:10.1021/acs.joc.6b01150

Explore citations to this article at