Polymer-supported stereoselective synthesis of tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-oxo-ethyl)-derivatized dipeptides via eastbound iminiums
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
23414200
DOI
10.1021/co3001567
Knihovny.cz E-resources
- MeSH
- Acetals chemistry MeSH
- Cyclization MeSH
- Dipeptides chemical synthesis chemistry MeSH
- Molecular Structure MeSH
- Oxazoles chemical synthesis chemistry MeSH
- Polymers chemistry MeSH
- Pyrazolones chemical synthesis chemistry MeSH
- Stereoisomerism MeSH
- Combinatorial Chemistry Techniques MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Acetals MeSH
- Dipeptides MeSH
- Oxazoles MeSH
- Polymers MeSH
- Pyrazolones MeSH
Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acylium ion cyclization-nucleophilic addition to yield tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.
References provided by Crossref.org
Traceless Solid-Phase Synthesis of [6,7,8 + 5,6,7]-Fused Molecular Frameworks
