Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds

被引：5

作者：

Listro, Roberta ^{[1
]}

Rossino, Giacomo ^{[1
]}

Della Volpe, Serena ^{[1
]}

Stabile, Rita ^{[1
]}

Boiocchi, Massimo ^{[2
]}

Malavasi, Lorenzo ^{[3
]}

Rossi, Daniela ^{[1
]}

Collina, Simona ^{[1
]}

机构：

[1] Univ Pavia, Dept Drug Sci, Via Taramelli 12, I-27100 Pavia, Italy

[2] Univ Pavia, Ctr Grandi Strumenti, Via Bassi 21, I-27100 Pavia, Italy

[3] Univ Pavia, Dept Chem, Via Taramelli 12, I-27100 Pavia, Italy

来源：

MOLECULES | 2020年 / 25卷 / 24期

关键词：

lactam scaffold; enantioselective HPLC; chiral resolution; X-ray diffraction; absolute configuration assignment; RNA-BINDING PROTEIN; CRYSTAL-STRUCTURE; DESIGN; CONDENSATION; SEPARATION; ASSIGNMENT; SCAFFOLDS; RECEPTOR; CANCER; SPACE;

D O I：

10.3390/molecules25246023

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

During the past several years, the frequency of discovery of new molecular entities based on gamma- or delta-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams.

引用

页数：15

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