title: Multicomponent Synthesis of Cyclic Depsipeptide Mimics by Ugi Reaction Including Cyclic Hemiacetals Derived from Asymmetric Organocatalysis.
abstract: The synthesis of novel cyclic depsipeptide mimics by means of an organocatalytic conjugate addition, leading to chiral cyclic hemiacetals, followed by a multicomponent reaction with α-amino acids and isocyanides, is described. The initial organocatalytic step is employed for the asymmetric derivatization of α,β-unsaturated aldehydes to 4,5-disubstituted 2-hydroxytetrahydropyrans, which are next used as chiral bifunctional substrates on the Ugi five-center three-component reaction, giving rise to nine-membered-ring lactones. This sequential approach proved to be suitable for the rapid generation of molecular complexity through the combination of aliphatic, dipeptidic, glucosidic, and lipidic isocyanides with several amino acids, thus giving access to amido-, glyco-, and lipo-depsipeptide scaffolds featuring natural product-like structures.
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos , São Carlos, SP, 13565-905, Brazil.
authors.forename: Alexander F
authors.initials: AF
authors.lastname: de la Torre
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos , São Carlos, SP, 13565-905, Brazil.|Center for Natural Products Research, Faculty of Chemistry, University of Havana , Zapata y G, 10400, La Habana, Cuba.
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Rivera
authors.affiliation: Center for Natural Products Research, Faculty of Chemistry, University of Havana , Zapata y G, 10400, La Habana, Cuba.
authors.forename: Odette
authors.initials: O
authors.lastname: Concepción
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos , São Carlos, SP, 13565-905, Brazil.|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: Echemendia
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos , São Carlos, SP, 13565-905, Brazil.
authors.forename: Arlene G
authors.initials: AG
authors.lastname: Correa
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos , São Carlos, SP, 13565-905, Brazil.
authors.forename: Márcio W
authors.initials: MW
authors.lastname: Paixão