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- Title
Completion of the Total Synthesis of Several Bioactive Sarpagine/Macroline Alkaloids including the Important NF-κB Inhibitor N<sub>4</sub>-Methyltalpinine.
- Authors
Toufiqur Rahman, Md.; Naga Phani Babu Tiruveedhula, Veera Venkata; Stephen, Michael Rajesh; Rallapalli, Sundari K.; Pandey, Kamal P.; Cook, James M.
- 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.
- Publication
Molecules, 2022, Vol 27, Issue 5, p1
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27051738