ChemInform Abstract: Development of Base-Catalyzed Diels-Alder Reaction of 3-Hydroxy-2-pyrone and Application to Synthesis of Biologically Active Compounds

ChemInform ◽  
2010 ◽  
Vol 30 (30) ◽  
pp. no-no
Author(s):  
Hiroaki Okamura ◽  
Testuo Iwagawa ◽  
Munehiro Nakatani
2011 ◽  
Vol 7 ◽  
pp. 1007-1013 ◽  
Author(s):  
Boubacar Sow ◽  
Gabriel Bellavance ◽  
Francis Barabé ◽  
Louis Barriault

The rapid synthesis of bicyclo[m.n.1]alkanone cores possessing quaternary carbon centers adjacent to a bridged ketone represents a significant synthetic challenge. This type of architectural feature is embedded in various complex biologically active compounds such as hyperforin and garsubellin A. Herein, we report a highly diastereoselective one-pot Diels–Alder reaction/Au(I)-catalyzed carbocyclization to generate bicyclo[3.3.1]alkanones in yields ranging from 48–93%.


2019 ◽  
Vol 16 (2) ◽  
pp. 205-243 ◽  
Author(s):  
Majid M. Heravi ◽  
Mahzad Dehghani ◽  
Vahideh Zadsirjan ◽  
Manijheh Ghanbarian

Background:Alkynes are actually basic chemicals, serving as privileged synthons for planning new organic reactions for assemblage of a reactive motif, which easily undergoes a further desirable transformation. Name reactions, in organic chemistry are referred to those reactions which are well-recognized and reached to such status for being called as their explorers, discoverers or developers. Alkynes have been used in various name reactions. In this review, we try to underscore the applications of alkynes as privileged synthons in prevalent name reactions such as Huisgen 1,3-dipolar cycloaddtion via Click reaction, Sonogashira reaction, and Hetero Diels-Alder reaction.Objective:In this review, we try to underscore the applications of alkynes as privileged synthons in the formation of heterocycles, focused on the selected reactions of alkynes as a synthon or impending utilization in synthetic organic chemistry, which have reached such high status for being included in the list of name reactions in organic chemistry.Conclusion:Alkynes (including acetylene) are an unsaturated hydrocarbon bearing one or more triple C-C bond. Remarkably, alkynes and their derivatives are frequently being used as molecular scaffolds for planning new organic reactions and installing reactive functional group for further reaction. It is worth mentioning that in general, the terminal alkynes are more useful and more frequently being used in the art of organic synthesis. Remarkably, alkynes have found different applications in pharmacology, nanotechnology, as well as being known as appropriate starting precursors for the total synthesis of natural products and biologically active complex compounds. They are predominantly applied in various name reactions such as Sonogashira, Glaser reaction, Friedel-crafts reaction, Castro-Stephens coupling, Huisgen 1.3-dipolar cycloaddtion reaction via Click reaction, Sonogashira reaction, hetero-Diels-Alder reaction. In this review, we tried to impress the readers by presenting selected name reactions, which use the alkynes as either stating materials or precursors. We disclosed the applications of alkynes as a privileged synthons in several popular reactions, which reached to such high status being classified as name reactions. They are thriving and well known and established name reactions in organic chemistry such as Regioselective, 1,3-dipolar Huisgen cycloaddtion reaction via Click reaction, Sonogashira reaction and Diels-Alder reaction.


Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1772
Author(s):  
Ignacio E. Tobal ◽  
Rocío Bautista ◽  
David Diez ◽  
Narciso M. Garrido ◽  
Pilar García-García

In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among the most important dienes are the cyclic dienes, as they facilitate the reaction. This review considers the synthesis and reactivity of one of these dienes with special characteristics—it is cyclic and has an electron withdrawing group. This building block has been used for the synthesis of biologically active compounds and is present in natural compounds with interesting properties.


Synlett ◽  
2020 ◽  
Vol 31 (10) ◽  
pp. 1007-1010
Author(s):  
Koichiro Ota ◽  
Hiroaki Miyaoka ◽  
Kazuo Kamaike

Herein, a concise strategy designed to provide general and diversifiable access to various prenyleudesmane terpenoids is described and utilized in the asymmetric synthesis of a biologically active prenyleudesmane diterpenoid, sinupol, which is accomplished in a seven-step procedure.


2019 ◽  
Vol 16 (11) ◽  
pp. 865-873 ◽  
Author(s):  
Palani Amudha ◽  
Gnanamani Lavanya ◽  
Karuppan Venkatapathy ◽  
Chinnian Jayaraman Magesh

A recyclable, eco-friendly, efficient method of synthesis has been developed for the biologically active heterocycles pyranoquinolines and furanoquinolines via inverse electron demand Diels- Alder reaction mediated by choline chloride: zinc chloride ionic liquid as a catalyst and medium. The methodology offers the advantages such as mild reaction conditions, simple work-up procedure, highly efficient reaction, recyclable and eco-friendly catalyst etc. All the products were thoroughly characterized by FT-IR, 1H-NMR, 13C-NMR, Mass spectral and Elemental analysis.


Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>


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