Enantioselective synthesis of pyrro[3,4-c]quinoline pseudo-natural products

被引：8
|
作者：
Liu, Jie [1 ,2 ]
Otte, Felix [3 ]
Strohmann, Carsten [3 ]
Waldmann, Herbert [1 ,2 ]
机构：
[1] Max Planck Inst Mol Physiol, Dept Chem Biol, Otto Hahn Str 11, D-44227 Dortmund, Germany
[2] Tech Univ Dortmund, Fac Chem Chem Biol, Otto Hahn Str 6, D-44221 Dortmund, Germany
[3] Tech Univ Dortmund, Fac Chem Inorgan Chem, Otto Hahn Str 6, D-44221 Dortmund, Germany
来源：
TETRAHEDRON LETTERS | 2021年 / 76卷
关键词：
Pseudo natural product; Pyrroquinoline; 1; 3-Dipolar cycloaddition; Asymmetric synthesis; BIOLOGY; CYCLOADDITION;
D O I：
10.1016/j.tetlet.2021.153228
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pseudo natural products (PNPs) are natural product-inspired compounds obtained by unprecedented combination of natural product (NP) fragments in complexity-generating transformations. The pyrrolidine- and tetrahydroquinoline fragments individually occur in numerous NPs with diverse bioactivity, yet not in combination. Herein we report the enantioselectively catalyzed asymmetric synthesis of pyrro [3,4-c]quinoline pseudo-natural products in which these two fragments are combined. The synthesis includes a highly enantioselective 1,3-dipolar cycloaddition between amino acid-derived azomethine ylides and alpha, beta-unsaturated malonic acid esters to yield pyrrolidines followed by a sequence of protection-, reduction- and lactamization steps. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：4
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