title: Highly stereoselective synthesis of natural-product-like hybrids by an organocatalytic/multicomponent reaction sequence.
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.
authors.affiliation: Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, 10400, La Habana (Cuba).
authors.forename: Radell
authors.initials: R
authors.lastname: Echemendía
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos, São Carlos, 97105-900, SP (Brasil).
authors.forename: Alexander F
authors.initials: AF
authors.lastname: de La Torre
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos, São Carlos, 97105-900, SP (Brasil).
authors.forename: Julia L
authors.initials: JL
authors.lastname: Monteiro
authors.affiliation: Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, 10400, La Habana (Cuba).
authors.forename: Michel
authors.initials: M
authors.lastname: Pila
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos, São Carlos, 97105-900, SP (Brasil).
authors.forename: Arlene G
authors.initials: AG
authors.lastname: Corrêa
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale) (Germany).|Martin-Luther-University, Halle Wittenberg, Institute of Chemistry, Kurt-Mothes-Str. 2, 06120 Halle (Germany).
authors.forename: Bernhard
authors.initials: B
authors.lastname: Westermann
authors.affiliation: Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, 10400, La Habana (Cuba). dgr@fq.uh.cu.
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Rivera
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos, São Carlos, 97105-900, SP (Brasil). mwpaixao@ufscar.br.
authors.forename: Márcio W
authors.initials: MW
authors.lastname: Paixão
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002241:Carbohydrates; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002241:Carbohydrates
keywords: carbohydrates; diversity-oriented synthesis; multicomponent reactions; organocatalysis; synthetic methods