scholarly journals Copper-Catalyzed Regioselective Synthesis of (E)-β-Fluorovinyl Sulfones

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1569 ◽  
Author(s):  
Raquel Román ◽  
Pablo Barrio ◽  
Natalia Mateu ◽  
Daniel M. Sedgwick ◽  
Santos Fustero

Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed (E)-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and E/Z selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related Z isomers. These new products may find interesting applications, given the versatility of vinyl sulfones in chemical synthesis and the unique properties of vinyl fluorides in biological settings.

Catalysts ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 471
Author(s):  
Eleonora Tosi ◽  
Renata Marcia de Figueiredo ◽  
Jean-Marc Campagne

The crucial role played by compounds bearing amide functions, not only in biological processes but also in several fields of chemistry, life polymers and material sciences, has brought about many significant discoveries and innovative approaches for their chemical synthesis. Indeed, a plethora of strategies has been developed to reach such moieties. Amides within chiral molecules are often associated with biological activity especially in life sciences and medicinal chemistry. In most of these cases, their synthesis requires extensive rethinking methodologies. In the very last years (2019–2020), enantioselective C-H functionalization has appeared as a straightforward alternative to reach chiral amides. Therein, an overview on these transformations within this timeframe is going to be given.


2006 ◽  
pp. 51-89 ◽  
Author(s):  
Steven V. Ley ◽  
Ian R. Baxendale ◽  
Deborah A. Longbottom ◽  
Rebecca M. Myers

2022 ◽  
Author(s):  
K. Lam ◽  
M. C. Leech ◽  
A. J. J. Lennox

The multistep synthesis of natural products has historically served as a useful and informative platform for showcasing the best, state-of-the-art synthetic methodologies and technologies. Over the last several decades, electrochemistry has proved itself to be a useful tool for conducting redox reactions. This is primarily due to its unique ability to selectively apply any oxidizing or reducing potential to a sufficiently conductive reaction solution. Electrochemical redox reactions are readily scaled and can be more sustainable than competing strategies based on conventional redox reagents. In this chapter, we summarize the examples where electrochemistry has been used in the synthesis of natural products. The chapter is organized by the reaction type of the electrochemical step and covers both oxidative and reductive reaction modes.


2019 ◽  
Vol 2019 ◽  
pp. 1-15 ◽  
Author(s):  
Merly de Armas-Ricard ◽  
Enrique Ruiz-Reyes ◽  
Oney Ramírez-Rodríguez

Polyphenols are secondary metabolites of plants and include a variety of chemical structures, from simple molecules such as phenolic acids to condensed tannins and highly polymerized compounds. Caffeic acid (3,4-dihydroxycinnamic acid) is one of the hydroxycinnamate metabolites more widely distributed in plant tissues. It is present in many food sources, including coffee drinks, blueberries, apples, and cider, and also in several medications of popular use, mainly those based on propolis. Its derivatives are also known to possess anti-inflammatory, antioxidant, antitumor, and antibacterial activities, and can contribute to the prevention of atherosclerosis and other cardiovascular diseases. This review is an overview of the available information about the chemical synthesis and antioxidant activity of caffeic acid derivatives. Considering the relevance of these compounds in human health, many of them have been the focus of reviews, taking as a center their obtaining from the plants. There are few revisions that compile the chemical synthesis methods, in this way, we consider that this review does an important contribution.


Author(s):  
Rishab N. Iyer ◽  
David Favela ◽  
Guoliang Zhang ◽  
David E. Olson

Few classes of natural products have inspired as many chemists and biologists as have the iboga alkaloids. This review covers recent advances in the biosynthesis and chemical synthesis of iboga alkaloids and their use as neurotherapeutics.


1993 ◽  
Vol 39 (2) ◽  
pp. 131-140 ◽  
Author(s):  
John B. Pillmoor ◽  
Kenneth Wright ◽  
Adrian S. Terry

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