scholarly journals Synthesis of Bioactive Fluoropyrrolidines via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides

2021 ◽  
Author(s):  
Xiao Xu ◽  
Longzhu Bao ◽  
Lu Ran ◽  
Zhenyan Yang ◽  
Dingce Yan ◽  
...  
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Biologically Active ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Active Natural

Chiral pyrrolidinyl units are important building blocks in biologically active natural products and drugs, and the develpment of efficient methods for the synthesis of diverse structured pyrrolidine derivatives is of...

scholarly journals Synthesis of Bioactive Fluoropyrrolidines via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides

2021 ◽  
Author(s):  
Xiao Xu ◽  
Longzhu Bao ◽  
Lu Ran ◽  
Zhenyan Yang ◽  
Dingce Yan ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Biological Activities ◽  
Building Blocks ◽  
Biologically Active ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Inhibition Rate ◽  
Efficient Route ◽  
High Yields ◽  
Structural Blocks

Abstract Chiral pyrrolidinyl units are important building blocks in biologically active natural products and drugs, thereupon, searching approaches for the synthesis of diverse structured pyrrolidine derivatives is of great importance. Meanwhile, owing to the special physicochemical properties of fluorine atoms, the introduction of fluorine containing groups into small molecules often change their activities to a great extent. Herein, we reported an efficient route to chiral 3,3-difluoro- and 3,3,4-trifluoropyrrodinyl derivatives by Cu(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides with less active 1,1-difluoro- and 1,1,2-trifluoroalkenes. A series of new fluorinated pyrrolidines have been prepared in high yields (up to 96%) and excellent stereoselectivities (up to > 20:1 dr and 97% ee), and these unique structural blocks could be readily introduced into some natural compounds and pharmaceuticals. Additionally, antifungal activity investigation against four common plant funguses showed that some products possess general and high biological activities (up to 93% inhibition rate), the comparison with the antifungal activities of corresponding non-fluorinated compounds (low to 13% inhibition rate) revealed that the fluorine atoms at pyrrolidinyl rings play a crucial role in the antifungal activity, which prove the special properties of fluorine atoms in organic molecules.

Biologically active natural products from Cassine viburnifolia

Planta Medica ◽  
2015 ◽  
Vol 81 (11) ◽  
Author(s):  
T Grkovic ◽  
R Akee ◽  
J Evans ◽  
JM Collins ◽  
B O'Keefe
Keyword(s):  
Natural Products ◽  
Biologically Active ◽  
Active Natural

Synthetic studies on biologically active natural products by a chemicoenzymatic approach

Tetrahedron ◽  
1984 ◽  
Vol 40 (1) ◽  
pp. 145-152 ◽  
Author(s):  
Masaji Ohno ◽  
Yukishige Ito ◽  
Masafumi Arita ◽  
Tomoyuki Shibata ◽  
Kunitomo Adachi ◽  
...  
Keyword(s):  
Natural Products ◽  
Biologically Active ◽  
Synthetic Studies ◽  
Active Natural

Back to the Roots: Prediction of Biologically Active Natural Products from Ayurveda Traditional Medicine

2011 ◽  
Vol 30 (2-3) ◽  
pp. 181-187 ◽  
Author(s):  
Honey Polur ◽  
Tejal Joshi ◽  
Christopher T. Workman ◽  
Gandhidas Lavekar ◽  
Irene Kouskoumvekaki
Keyword(s):  
Natural Products ◽  
Traditional Medicine ◽  
Biologically Active ◽  
Active Natural

The Exploitation of Enzymatically-Derivedcis-1,2-Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

2017 ◽  
Vol 18 (2) ◽  
pp. 239-264 ◽  
Author(s):  
Ehab S. Taher ◽  
Martin G. Banwell ◽  
Joshua N. Buckler ◽  
Qiao Yan ◽  
Ping Lan
Keyword(s):  
Natural Products ◽  
Biologically Active ◽  
Related Compounds ◽  
Active Natural
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