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

被引：12
|
作者：
La Venia, Agustina [1 ,3 ]
Dolensky, Bohumil [2 ]
Krchnak, Viktor [1 ,3 ]
机构：
[1] Palacky Univ, Fac Sci, Dept Organ Chem, Olomouc 77146, Czech Republic
[2] Inst Chem Technol, Dept Analyt Chem, CR-16628 Prague, Czech Republic
[3] Univ Notre Dame, Dept Chem & Biochem, Nieuwland Sci Ctr 251, Notre Dame, IN 46556 USA
来源：
ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 03期
关键词：
fused heterocycles; iminium; solid-phase synthesis; stereoselectivity; SOLID-PHASE SYNTHESIS; INTERMOLECULAR ADDITION-REACTIONS; ASYMMETRIC-SYNTHESIS; PEPTIDOMIMETICS; DIVERSITY;
D O I：
10.1021/co3001567
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
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 fay 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.
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页码：162 / 167
页数：6
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