A multicomponent approach to the synthesis of 1,3-dicarbonylic compounds
- 3 September 2010
- journal article
- research article
- Published by Springer Nature in Molecular Diversity
- Vol. 15 (2) , 529-539
Abstract
A general synthesis of 1,3-dicarbonylic compounds using multicomponent reactions of isocyanides is described. The process involves a Passerini three-component condensation of glyoxal derivatives, isocyanides and acetic acid, followed by metal mediated reductive or solvolytic removal of the acid component. Noteworthy, reductive deacetoxylation of Passerini glyoxylamide adducts was successfully achieved using photochemically activated SmI2. This procedure constitutes a novel convenient method for the direct synthesis of malonic retro-peptidic subunits.Keywords
This publication has 47 references indexed in Scilit:
- Peptidomimetics, a synthetic tool of drug discoveryCurrent Opinion in Chemical Biology, 2008
- The partial retro–inverso modification: A road traveled togetherPeptide Science, 2005
- Partially Modified Retro-Inverso Peptides: Development, Synthesis, and Conformational BehaviorChemical Reviews, 1998
- Multicomponent reactions in organic chemistryEndeavour, 1994
- Concepts and progress in the development of peptide mimeticsJournal of Medicinal Chemistry, 1993
- Synthesis, biological testing, and stereochemical assignment of an end group modified retro-inverso bombesin C-terminal nonapeptideThe Journal of Organic Chemistry, 1990
- Synthesis of partially modified retro-inverso substance P analogs and their biological activityJournal of Medicinal Chemistry, 1983
- Preparation of optically pure monoacyl 2-alkyl gem-diamines from peptide amidesJournal of the Chemical Society, Chemical Communications, 1982
- On the concept of linear modified retro-peptide structuresAccounts of Chemical Research, 1979
- A general approach to retro-isomeric linear peptide synthesisJournal of the American Chemical Society, 1977