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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Highly Stereoselective Synthesis of Natural-Product-Like Hybrids by an Organocatalytic/Multicomponent Reaction Sequence

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Echemendia, Radell [1] ; de La Torre, Alexander F. [2] ; Monteiro, Julia L. [2] ; Pila, Michel [1] ; Correa, Arlene G. [2] ; Westermann, Bernhard [3, 4] ; Rivera, Daniel G. [1] ; Paixao, Marcio W. [2]
Total Authors: 8
[1] Univ Havana, Ctr Nat Prod Res, Fac Chem, Havana 10400 - Cuba
[2] Univ Fed Sao Carlos, Dept Quim, BR-97105900 Sao Carlos, SP - Brazil
[3] Univ Halle Wittenberg, Inst Chem, D-06120 Halle - Germany
[4] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale - Germany
Total Affiliations: 4
Document type: Journal article
Source: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 54, n. 26, p. 7621-7625, JUN 22 2015.
Web of Science Citations: 29

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 ,-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. (AU)

FAPESP's process: 13/21599-8 - Multicomponent organocatalytic strategies to anticancer natural products
Grantee:Arlene Gonçalves Corrêa
Support type: Research Grants - Visiting Researcher Grant - International