Short and efficient diastereoselective synthesis of pyrrolidinone-containing dipeptide analogues

Abstract

The pyrrolidine-2,4-diones have been identified as a convenient starting point for the synthesis of peptide analogues. Herein we describe an optimized two-step reductive amination procedure, which provides a small library of pyrrolidinone-containing dipeptide analogues in high yield and excellent diastereoselectivity.

Metal-Catalyzed and Metal-Mediated Approaches to the Synthesis and Functionalization of Tetramic Acids

“…Reutericyclin, tenuazonic acid, streptolydigin, and equisetin are representative examples of biologically active natural products, whereas the most wellknown commercial product is the insecticidal spirocyclic tetramic acid spirotetramat [15] (Figure 1). (Figure 3; Part A) [31], 3-amino-pyrrolidinone dipeptides [32], and tripeptides [33] that contributed to the research of peptidomimetics bearing tetramate analogues [34,35]. More recently, Lee et al prepared ampicillin, cephalosporin, cephamycin, and other β-lactam-tetramic acid hybrids, and evaluated their antimicrobial activity (Figure 3; Part B) [36,37].…”

The Syntheses Of Fused Cyclic 5/6-Membered Ring Lactams Via Enamine Hydrogenation

“…Among a list of the produced reaction products of our prior work (Mohammat et al, 2012), compound 1a and 1b were nominated. After an effort to reductive amination (Hosseini et al, 2007) of 1a…”

Studies on the Synthesis and Bioactivities of 4‐Amino Derivatives of Tetramic Acid

“…Acetic acid was finally shown to be suitable for the task. Referring to the reaction condition of tetramic acid reacting with amino acid , the 4‐amination of 5b was conducted in a mixture of ethanol and acetic acid and gave the 4‐amination product 6b in 69% yield. Reacting 5a , 5b , 5c with different amines under the same conditions afforded 6a , 6b , 6c , 6d , 6e , 6f , 6g , 6h , 6i , 6j , 6k , 6l , 6m , 6n , 6o in 52% to 74% yields (Scheme ).…”