Highly Stereoselective Synthesis of Natural‐Product‐Like Hybrids by an Organocatalytic/Multicomponent Reaction Sequence |
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| Authors: | M. Sc. Radell Echemendía M. Sc. Alexander F. de La Torre M. Sc. Julia L. Monteiro M. Sc. Michel Pila Prof. Dr. Arlene G. Corrêa Prof. Dr. Bernhard Westermann Prof. Dr. Daniel G. Rivera Prof. Dr. Márcio W. Paixão |
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| Affiliation: | 1. Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, 10400, La Habana (Cuba);2. Departamento de Química, Universidade Federal de S?o Carlos, S?o Carlos, 97105‐900, SP (Brasil);3. Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale) (Germany);4. Martin‐Luther‐University, Halle Wittenberg, Institute of Chemistry, Kurt‐Mothes‐Str. 2, 06120 Halle (Germany) |
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| Abstract: | In an endeavor to provide an efficient route to natural product hybrids, described herein is an efficient, highly stereoselective, one‐pot process comprising an organocatalytic conjugate addition of 1,3‐dicarbonyls to α,β‐unsaturated aldehydes followed by an intramolecular isocyanide‐based multicomponent reaction. This approach enables the rapid assembly of complex natural product hybrids including up to four different molecular fragments, such as hydroquinolinone, chromene, piperidine, peptide, lipid, and glycoside moieties. The strategy combines the stereocontrol of organocatalysis with the diversity‐generating character of multicomponent reactions, thus leading to structurally unique peptidomimetics integrating heterocyclic, lipidic, and sugar moieties. |
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| Keywords: | carbohydrates diversity‐oriented synthesis multicomponent reactions organocatalysis synthetic methods |
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