N-Carboxyanhydrides directly from amino acids and carbon dioxide and their tandem reactions to therapeutic alkaloids. Issue 23 (10th November 2022)

• Record Type: Journal Article
• Authors: Tran, Thi V.; Shen, Yi; Nguyen, Hieu D.; Deng, Shijie; Roshandel, Hootan; Cooper, Mason M.; Watson, Jose R.; Byers, Jeffery A.; Diaconescu, Paula L.; Do, Loi H.
• Is Part Of: Green chemistry. Volume 24:Issue 23(2022)
• Page Start: 9245
• Page End: 9252
• Publication Date: 2022-11-10
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc03507c
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : A phosgene-free method to prepare N -carboxyanhydrides from amino acids and carbon dioxide has been developed. This method is mild enough to be used in the tandem synthesis of alkaloids tryptanthrin and phaitanthrin A. Abstract : We report on the preparation of synthetically versatile N -carboxyanhydrides (NCAs) directly from amino acids and CO2 using n -propylphosphonic anhydride. Most of the NCAs were isolated with >95% purity after simple workup, avoiding the need for tedious purification procedures typically required using conventional methods. Because the reagents and conditions employed are mild, tandem reactions with moisture-sensitive NCAs were carried out to transform them into the medicinally active alkaloids tryptanthrin and phaitanthrin A in one pot. A qualitative analysis revealed that our NCA synthesis approach is more green than conventional methods, which all directly or indirectly use the highly poisonous gas phosgene.