1. N-Carboxyanhydrides directly from amino acids and carbon dioxide and their tandem reactions to therapeutic alkaloids.
- Author
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Tran, Thi V., Shen, Yi, Nguyen, Hieu D., Deng, Shijie, Roshandel, Hootan, Cooper, Mason M., Watson, Jose R., Byers, Jeffery A., Diaconescu, Paula L., and Do, Loi H.
- Subjects
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AMINO acids , *CARBON dioxide , *POISONOUS gases , *PHOSGENE , *ALKALOIDS , *CHEMICAL purification - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2022
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