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Highly Stereoselective Synthesis of Natural‐Product‐Like Hybrids by an Organocatalytic/Multicomponent Reaction Sequence
Author(s) -
Echemendía Radell,
de La Torre Alexander F.,
Monteiro Julia L.,
Pila Michel,
Corrêa Arlene G.,
Westermann Bernhard,
Rivera Daniel G.,
Paixão Márcio W.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201412074
Subject(s) - chemistry , stereoselectivity , natural product , organocatalysis , ugi reaction , peptidomimetic , combinatorial chemistry , intramolecular force , michael reaction , organic chemistry , piperidine , stereochemistry , enantioselective synthesis , isocyanide , catalysis , peptide , biochemistry
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.