Glycal mediated synthesis of piperidine alkaloids: fagomine, 4-epi-fagomine, 2-deoxynojirimycin, and an advanced intermediate, iminoglycal

TitleGlycal mediated synthesis of piperidine alkaloids: fagomine, 4-epi-fagomine, 2-deoxynojirimycin, and an advanced intermediate, iminoglycal
Publication TypeJournal Article
Year of Publication2022
AuthorsChand, HR, Tiwari, MK, Bhattacharya, AK
JournalRSC Advances
Volume12
Issue51
Pagination33021-33031
Date PublishedNOV
Type of ArticleArticle
Abstract

Glucal and galactal are transformed into 2-deoxyglycolactams, which are important building blocks in the synthesis of biologically active piperidine alkaloids, fagomine and 4-epi-fagomine. In one of the strategies, reduction of 2-deoxyglycolactam-N-Boc carbonyl by lithium triethylborohydride (Super-Hydride (R)) has been exploited to generate lactamol whereas reduction followed by dehydration was utilized as the other strategy to functionalize the C-1-C-2 bond in the iminosugar substrate. The strategies provide the formal synthesis of 2-deoxynojirimycin, nojirimycin and nojirimycin B. DFT studies were carried out to determine the reason for the failure of the formation of the 2-deoxygalactonojirimycin derivative. Further, DFT studies suggest that phenyl moieties of protecting groups and lone pairs of oxygen in carbamate group plays a vital role in deciphering the conformational space of the reaction intermediates and transition-state structures through cation-pi or cation-lone pair interactions. The influence of these interactions is more pronounced at low temperature when the entropy factor is small.

DOI10.1039/d2ra05224e
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.036

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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