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Completion of the Total Synthesis of Several Bioactive Sarpagine/Macroline Alkaloids including the Important NF-κB Inhibitor N4-Methyltalpinine

Authors :
Md Toufiqur Rahman
Veera Venkata Naga Phani Babu Tiruveedhula
Michael Rajesh Stephen
Sundari K. Rallapalli
Kamal P. Pandey
James M. Cook
Source :
Molecules, Vol 27, Iss 5, p 1738 (2022)
Publication Year :
2022
Publisher :
MDPI AG, 2022.

Abstract

The unification of the general synthetic strategy regarding the important and emerging group of C-19 methyl-substituted sarpagine/macroline alkaloids has culminated in the completion of the total synthesis of several bioactive alkaloids. Key transformations include an ACE-Cl mediated late-stage N(4)-demethylation and an anhydrous acid-mediated intramolecular quaternary hemiaminal formation between a tertiary amine and an aldehyde function to allow efficient access to several biologically important alkaloids from this group. Herein, the enantiospecific total synthesis of the first known sarpagine/macroline alkaloid with NF-κB inhibitory activity, N(4)-methyltalpinine (as a chloride salt), as well as the anticancer alkaloids talpinine, O-acetyltalpinine, and macrocarpines F–G, are described.

Details

Language :
English
ISSN :
14203049
Volume :
27
Issue :
5
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.9faea352b388405580b76cb1c2e0624e
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules27051738