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
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
23414200
DOI
10.1021/co3001567
Knihovny.cz E-zdroje
- MeSH
- acetaly chemie MeSH
- cyklizace MeSH
- dipeptidy chemická syntéza chemie MeSH
- molekulární struktura MeSH
- oxazoly chemická syntéza chemie MeSH
- polymery chemie MeSH
- pyrazolony chemická syntéza chemie MeSH
- stereoizomerie MeSH
- techniky kombinatorické chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- acetaly MeSH
- dipeptidy MeSH
- oxazoly MeSH
- polymery MeSH
- pyrazolony 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.
Citace poskytuje Crossref.org
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