Design and synthesis of a new chiral macrocyclic dilactam and its characterization by NMR and single-crystal X-ray diffraction

被引：0

作者：

Sanchez-Perez, Divina P. ^{[1
]}

Gomez-Calvario, Victor ^{[2
]}

Jimenez, Jacqueline ^{[2
]}

Velasco, Manuel ^{[1
]}

Mendoza, Angel ^{[1
]}

Juarez, Jorge R. ^{[1
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Inst Ciencias, Ctr Quim, Edif IC-9,Complejo Ciencias CU, Puebla 72570, Pue, Mexico

[2] Benemerita Univ Autonoma Puebla, Fac Ciencias Quim, Puebla 72570, Mexico

来源：

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY | 2024年

关键词：

Alkaloids; Macrocyclic dilactam; Synthesis; (<italic>R</italic>)-phenylglycinol; CROWN-ETHERS; DERIVATIVES; CHEMISTRY;

D O I：

10.1007/s10847-024-01271-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this study, we report the synthesis and structural characterization of a new chiral macrocyclic dilactam (1) using (R)-phenylglycinol as a key building block. Macrocyclic polyether dilactams, such as this compound, have garnered attention for their ability to form complexes with cations, anions, heavy-metal ions, and neutral organic molecules, displaying potential biological applications as molecular or ion receptors and antibiotics. Building on our expertise in synthesizing chiral piperidine derivatives for alkaloid synthesis, we employed efficient diastereoselective strategies to develop this macrocycle. The complete structural assignment, crucial for correlating structural patterns with biological activity, was achieved through two-dimensional NMR spectroscopy and X-ray diffraction analysis. This work provides valuable insights into the design of diaza-crown ethers with potential applications in supramolecular systems and medicinal chemistry.

引用

页码：159 / 166

页数：8