Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products

2002 ◽  
Keyword(s):  
Natural Products ◽  
Dipolar Cycloaddition

Glycoconjugation of 4-Methylumbelliferone via “Click Chemistry”

2014 ◽  
Vol 881-883 ◽  
pp. 414-418
Author(s):  
Ru Chun Yang ◽  
Tao Hu ◽  
Ban Peng Cao ◽  
Xi Chen ◽  
Qiang Xiao
Keyword(s):  
Natural Products ◽  
Click Chemistry ◽  
High Yield ◽  
Dipolar Cycloaddition ◽  
Derivatives Of

A series of carbohydrate-conjugated 4-methylumbelliferone were synthesized using 1,3-dipolar cycloaddition “click chemistry” of the azide and alkyne. The reaction is straight forward and in high yield. The strategy will be useful for synthesizing glycoconjugated derivatives of natural products.

Recent Advances in the Chemistry of Doubly Activated Cyclopropanes: Synthesis and Reactivity

2019 ◽  
Vol 23 (3) ◽  
pp. 276-312 ◽  
Author(s):  
Purushothaman Gopinath ◽  
Srinivasan Chandrasekaran
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Electron Donor ◽  
Ring Opening ◽  
Dipolar Cycloaddition ◽  
Recent Advances ◽  
Donor Acceptor ◽  
Synthesis Reactions ◽  
Donor Substituent ◽  
Electron Donor Substituent

Diactivated cyclopropanes containing two geminal electron withdrawing groups, commonly called as ‘Doubly Activated Cyclopropanes’ are useful synthons for the synthesis of many interesting natural products and functionalized molecules. These geminal electron withdrawing groups (EWG’s) facilitate the regioselective ring opening of cyclopropanes by polarizing the C-C bond adjacent to it. This polarization also allows them to undergo 1,3 dipolar cycloaddition reactions when substituted with a suitable electron donor substituent at the adjacent carbon (donor-acceptor cyclopropanes) in the presence of suitable dipolarophiles. In this review, we discuss the recent advances in the chemistry of doubly activated cyclopropanes: their synthesis, reactions and applications in total synthesis.

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...

1,3-Dipolar cycloaddition of nitrones: synthesis of multisubstituted, diverse range of heterocyclic compounds

2021 ◽  
Author(s):  
Seema Thakur ◽  
Arunima Das ◽  
Tapas Das
Keyword(s):  
Natural Products ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Diverse Range

The 1,3-dipolar cycloaddition reaction of nitrone is one of the most important methods for the synthesis of different sizes of heterocycles which have enormous applications in natural products, biologically active molecules and pharmaceuticals.

Biology-Oriented Synthesis of Decahydro-4,8-epoxyazulene Scaffolds

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2918-2922 ◽  
Author(s):  
Zhi-Jun Jia ◽  
Christian Merten ◽  
Lena Knauer ◽  
Sandip Murarka ◽  
Carsten Strohmann ◽  
...  
Keyword(s):  
Natural Products ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Bioactive Natural Products ◽  
High Yields

Guided by the principle of biology-oriented synthesis, a collection of compounds with decahydro-4,8-epoxyazulene scaffold occurring in bioactive natural products was synthesized by the rhodium(II)-catalyzed 1,3-dipolar cycloaddition reaction of pentafulvenes and carbonyl ylides. The products can be obtained in moderate to high yields, with moderate enantioselectivity and excellent diastereoselectivity and regioselectivity.

Spiropyrazolines: A Worthy Insight into the Recent Strategies and Synthetic Applications

2019 ◽  
Vol 16 (5) ◽  
pp. 357-391
Author(s):  
Zubi Sadiq ◽  
Sadia Naz ◽  
Erum Akbar Hussain ◽  
Umbreen Aslam
Keyword(s):  
Natural Products ◽  
Structural Diversity ◽  
Dipolar Cycloaddition ◽  
Molecular Architecture ◽  
Pharmacological Activities ◽  
Insight Into ◽  
Biological And Pharmacological Activities

The structural diversity of spiro heterocycles has achieved an extensive attention of organic chemists due to their vast synthetic applications. Among these, spiropyrazolines are gaining considerable prominence due to their biological and pharmacological activities, electrophotographic photosensitivity as well as their application as beneficial synthons for spirocyclopropanes, cyclobutanes, pyrrolidinones, pyrazoles, 3-amino oxindoles and several natural products molecular architecture. In view of all these, this review aims to provide the classical and advanced regioselective approaches as well as synthetic applications of spiropyrazolines. The key reactions for its synthesis are 1,3-dipolar cycloaddition and condensations that are described completely in this piece of work.

Synthesis of Spiro-Isoxazolidine Derivatives of Methyl α-Isocostate

2019 ◽  
Vol 9 (4) ◽  
pp. 262-267
Author(s):  
Mohamed Zaki ◽  
Abdelouahd Oukhrib ◽  
Mohammed Loubidi ◽  
Ahmed El Hakmaoui ◽  
Marie-Aude Hiebel ◽  
...  
Keyword(s):  
Natural Products ◽  
Therapeutic Agents ◽  
Spiro Compounds ◽  
Dipolar Cycloaddition ◽  
Exocyclic Double Bond ◽  
Plant Resources ◽  
Enantiomerically Pure ◽  
Dittrichia Viscosa ◽  
Spiro Derivatives ◽  
Derivatives Of

Background: In recent decades, natural products are an important source of chemotherapeutics as more than half of the effective cancer drugs can be traced to natural origins. Objective: Moreover, the modification of natural products is one of the most common and fruitful approaches to obtain novel therapeutic agents in medicinal chemistry. Method: Continuing with a research project based on the support of Moroccan plant resources. we report herein the use of α-isocostic acid extracted in enantiomerically pure form from Dittrichia viscosa as a convenient starting material for the synthesis of new eudesmane derivatives. Results: Novel spiro derivatives with a natural scaffold were prepared. Spiro-isoxazolidine derivatives were generated on the exocyclic double bond adjacent to the ester α,β-unsaturated function by 1,3-dipolar cycloaddition of methyl α-isocostate 1 derived from sesquiterpenic isocostic acid, with nitrones 2. Conclusion: This procedure allowed us to generate enantiomerically pure spiro compounds in one diastereoisomer form with a limited number of steps. These compounds were fully characterized by spectroscopic methods.

Sign in / Sign up

Export Citation Format

Share Document