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ACS Comb Sci. 2014 Jul 14;16(7):359-66. doi: 10.1021/co500023k. Epub 2014 Apr 29.

Privileged structures as peptide backbone constraints: polymer-supported stereoselective synthesis of benzimidazolinopiperazinone peptides.

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Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17 Listopadu 12, 771 46 Olomouc, Czech Republic.


A molecular scaffold comprising a privileged structure was designed and synthesized to serve as a peptide backbone conformational constraint. The synthesis of highly functionalized 2,3,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-4(1H)-ones on a solid-phase support was performed via a tandem N-acyl-N-aryliminium ion cyclization-nucleophilic addition reaction. The synthesis proceeded with full stereocontrol of the newly formed stereogenic center. Conventional and microwave-assisted syntheses were compared with respect to efficiency and the optical integrity of the target compounds. Significant epimerization was observed during acylation with (S)- and (R)-2-bromopropionic acids under microwave conditions.

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