Total synthesis of α-1-C-propyl-3, 6-di-epi-nojirimycin and polyhydroxyindolizidine alkaloids via regio- and diastereoselective amination of anomeric acetals. (18th June 2022)

• Record Type: Journal Article
• Authors: Kim, Yeon Su; Boggu, Pulla Reddy; Kong, Younggyu; Park, Gi Min; Kim, In Su; Jung, Young Hoon
• Is Part Of: Tetrahedron. Volume 116(2022)
• Publication Date: 2022-06-18
• Subjects: Amination -- Chlorosulfonyl isocyanate -- α-1-C-Propyl-3, 6-di-epi-nojirimycin -- Polyhydroxyindolizidine alkaloids; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132809
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The synthesis of α-1- C -propyl-3, 6-di- epi -nojirimycin and Polyhydroxyindolizidine alkaloids from readily available α-methyl- d -mannopyranoside is described. The key step in this process involves a regioselective and diastereoselective amination of anomeric acetal functionality using chlorosulfonyl isocyanate (CSI). Graphical abstract: Image 1 Highlights: Total synthesis of α-1- C -Propyl-3, 6-di- epi -nojirimycin and polyhydroxyindolizidine Alkaloids. Regio-and diastereoselective amination of anomeric acetals using chlorosulfonyl isocyanate. SN i mechanism leading to retention of stereochemistry.