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

被引：1

作者：

Rahman, Md Toufiqur ^{[1
]}

Tiruveedhula, Veera Venkata Naga Phani Babu ^{[1
]}

Stephen, Michael Rajesh ^{[1
]}

Rallapalli, Sundari K. ^{[1
]}

Pandey, Kamal P. ^{[1
]}

Cook, James M. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem & Biochem, Milwaukee, WI 53211 USA

来源：

MOLECULES | 2022年 / 27卷 / 05期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

sarpagine alkaloids; macroline alkaloids; macrocarpine F; macrocarpine G; talpinine; O-acetyltalpinine; N(4)-methyltalpinine; NF-kappa B inhibitor; anticancer alkaloids; N-dealkylation; bioactive alkaloids; ENANTIOSPECIFIC TOTAL-SYNTHESIS; INDOLE ALKALOIDS; SARPAGINE; DERIVATIVES; BISINDOLE;

D O I：

10.3390/molecules27051738

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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-kappa B inhibitory activity, N(4)-methyltalpinine (as a chloride salt), as well as the anticancer alkaloids talpinine, O-acetyltalpinine, and macrocarpines F-G, are described.

引用

页数：18