Asymmetric cyclopropanation of chiral (1-phosphoryl)vinyl sulfoxides: A new approach to constrained analogs of biologically active compounds

2005 ◽  
Vol 77 (12) ◽  
pp. 2091-2098 ◽  
Author(s):  
Marian Mikołajczyk
Keyword(s):  
Transition State ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Theoretical Calculations ◽  
Experimental Results ◽  
Biologically Active ◽  
Active Compounds ◽  
New Approach ◽  
Cyclic Analog ◽  
Asymmetric Cyclopropanation

This account outlines the results obtained in the author's laboratory on the asymmetric cyclopropanation of enantiopure 1-phosphorylvinyl p-tolyl sulfoxides with sulfur ylides and diazoalkanes. Based on experimental results and theoretical calculations, the transition-state model for asymmetric cyclopropanation is proposed. A great synthetic value of the reaction investigated is exemplified by the total synthesis of constrained analogs of bioactive compounds, namely, enantiopure cyclic analog of phaclofen and cyclopropylphosphonate analogs of nucleotides.

Nickel(II)- and Silver(I)-Catalyzed C–H Bond Halogenation of Anilides and Carbamates

Synthesis ◽  
2020 ◽  
Author(s):  
Ebrahim Kianmehr ◽  
Hadi Afaridoun
Keyword(s):  
Biologically Active Compounds ◽  
Biologically Active ◽  
Silver Catalyst ◽  
Active Compounds ◽  
Available N ◽  
New Approach

Abstract ortho-C–H bond halogenation of anilides and N-aryl carbamates using easily available N-halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.

Asymmetric Organocatalytic Syntheses of Bioactive Compounds

2021 ◽  
Vol 18 ◽  
Author(s):  
Estibaliz Sansinenea ◽  
Aurelio Ortiz
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Cascade Reactions ◽  
Biologically Active ◽  
Active Compounds ◽  
Total Syntheses ◽  
Main Structure ◽  
New Methodologies ◽  
High Stereoselectivity

Background: The total syntheses of complex natural products have evolved to include new methodologies to save time, simplifying the form to achieve these natural compounds. Objective: In this review, we have described the asymmetric synthesis of different natural products and biologically active compounds of the last ten years until the current day. Results: An asymmetric organocatalytic reaction is the key to generate stereoselectively the main structure with the required stereochemistry. Conclusion: Even more remarkable, the organocatalytic cascade reactions, which are carried out with high stereoselectivity, as well as a possible approximation of the organocatalysts activation with substrates are also described.

scholarly journals Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

2014 ◽  
Vol 10 ◽  
pp. 1848-1877 ◽  
Author(s):  
Thilo Focken ◽  
Stephen Hanessian
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Biologically Active ◽  
Bond Forming ◽  
Michael Additions ◽  
Bond Forming Reactions ◽  
Asymmetric Alkylations

A review of the synthesis of natural products and bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be summarized, as well as an overview of the synthesis of the employed phosphonamide reagents.

Stereoselective strategies for the construction of polysubstituted piperidinic compounds and their applications in natural products’ synthesis

2017 ◽  
Vol 4 (8) ◽  
pp. 1655-1704 ◽  
Author(s):  
Nishanth Kandepedu ◽  
Isabelle Abrunhosa-Thomas ◽  
Yves Troin
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Natural Products Synthesis

An abridged and far-reaching review communication on the construction of the polysubstituted piperidinic core using diverse methodologies for the benefit of organic chemists interested in the total synthesis of biologically active compounds.

scholarly journals Organocatalytic Name Reactions Enabled by NHCs

Materials ◽  
2020 ◽  
Vol 13 (16) ◽  
pp. 3574
Author(s):  
Krzysztof Dzieszkowski ◽  
Izabela Barańska ◽  
Karina Mroczyńska ◽  
Michał Słotwiński ◽  
Zbigniew Rafiński
Keyword(s):  
Organic Chemistry ◽  
Total Synthesis ◽  
Heterocyclic Carbenes ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Great Opportunity

Giving reactions the names of their discoverers is an extraordinary tradition of organic chemistry. Nowadays, this phenomenon is much rarer, although already named historical reactions are still often developed. This is also true in the case of a broad branch of N‑heterocyclic carbenes catalysis. NHCs allow many unique synthetic paths, including commonly known name reactions. This article aims to gather this extensive knowledge and compare historical reactions with current developed processes. Furthermore, this review is a great opportunity to highlight some of the unique applications of these procedures in the total synthesis of biologically active compounds. Hence, this concise article may also be a source of knowledge for scientists just starting their adventure with N‑heterocyclic carbene chemistry.

scholarly journals Fungi and Algae as Sources of Medicinal and Other Biologically Active Compounds: A Review

Nutrients ◽  
2021 ◽  
Vol 13 (9) ◽  
pp. 3178
Author(s):  
Joanna Ślusarczyk ◽  
Edyta Adamska ◽  
Joanna Czerwik-Marcinkowska
Keyword(s):  
Bioactive Compounds ◽  
Nutritional Value ◽  
Human Life ◽  
Pharmaceutical Preparations ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Lichenized Fungi ◽  
Food Sources ◽  
Active Compounds ◽  
Therapeutic Properties

Many species of fungi including lichenized fungi (lichens) and algae have the ability to biosynthesize biologically active compounds. They produce, among others, polysaccharides with anticancer and immunostimulatory properties: (1) Background: This paper presents the characteristics of the most important bioactive compounds produced by fungi and algae; (2) Methods: Based on the example of the selected species of mushrooms, lichens and algae, the therapeutic properties of the secondary metabolites that they produce and the possibilities of their use are presented; (3) Results: The importance of fungi, especially large-fruited mushrooms, lichens and algae, in nature and human life is discussed, in particular, with regard to their use in the pharmaceutical industry and their nutritional value; (4) Conclusions: The natural organisms, such as fungi, lichenized fungi and algae, could be used as supplementary medicine, in the form of pharmaceutical preparations and food sources. Further advanced studies are required on the pharmacological properties and bioactive compounds of these organisms.

scholarly journals Ag2O versus Cu2O in the Catalytic Isomerization of Coordinated Diaminocarbenes to Formamidines: A Theoretical Study

Materials ◽  
2022 ◽  
Vol 15 (2) ◽  
pp. 491
Author(s):  
Juan F. Van der Maelen ◽  
Javier Ruiz
Keyword(s):  
Reaction Mechanism ◽  
Nitrogen Atom ◽  
Carbon Atom ◽  
Transition State ◽  
Theoretical Study ◽  
Theoretical Calculations ◽  
Experimental Results ◽  
Similar Reaction ◽  
Isomerization Process ◽  
Catalytic Isomerization

DFT theoretical calculations for the Ag2O-induced isomerization process of diaminocarbenes to formamidines, coordinated to Mn(I), have been carried out. The reaction mechanism found involves metalation of an N-H residue of the carbene ligand by the catalyst Ag2O and the formation of a key transition state showing a μ-η2:η2 coordination of the formamidinyl ligand between manganese and silver, which allows a translocation process of Mn(I) and silver(I) ions between the carbene carbon atom and the nitrogen atom, before the formation of the formamidine ligand is completed. Calculations carried out using Cu2O as a catalyst instead of Ag2O show a similar reaction mechanism that is thermodynamically possible, but highly unfavorable kinetically and very unlikely to be observed, which fully agrees with experimental results.

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