scholarly journals Synthetic Strategies in the Preparation of Phenanthridinones

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5560
Author(s):  
Rajeshwar Reddy Aleti ◽  
Alexey A. Festa ◽  
Leonid G. Voskressensky ◽  
Erik V. Van der Eycken

Phenanthridinones are important heterocyclic frameworks present in a variety of complex natural products, pharmaceuticals and displaying wide range of pharmacological actions. Its structural importance has evoked a great deal of interest in the domains of organic synthesis and medicinal chemistry to develop new synthetic methodologies, as well as novel compounds of pharmaceutical interest. This review focuses on the synthesis of phenanthridinone scaffolds by employing aryl-aryl, N-aryl, and biaryl coupling reactions, decarboxylative amidations, and photocatalyzed reactions.

2021 ◽  
Vol 9 ◽  
Author(s):  
K. Vipin Raj ◽  
Pawan S. Dhote ◽  
Kumar Vanka ◽  
Chepuri V. Ramana

Gold-catalysis, in this century, is one of the most emerging and promising new areas of research in organic synthesis. During the last two decades, a wide range of distinct synthetic methodologies have been unveiled employing homogeneous gold catalysis and aptly applied in the synthesis of numerous natural products and biologically active molecules. Among these, the reactions involving α-oxo gold carbene/α-imino gold carbene intermediates are of contemporary interest, in view of their synthetic potential and also due to the need to understand the bonding involved in these complexes. In this manuscript, we document the theoretical investigations on the regio-selectivity dependence of substitution on the gold-catalyzed cycloisomerization of o-nitroarylalkyne derivatives. We have also studied the relative stabilities of α-oxo gold carbene intermediates.


2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.


Author(s):  
Mengyu Qiu ◽  
Xuegang Fu ◽  
Peng Fu ◽  
Jianhui Huang

N-heterocycles can be found in natural products and drug molecules, which are indispensable components in the area of organic synthesis, medicinal chemistry and material science. The construction of these N-containing...


Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1342-1352 ◽  
Author(s):  
Javier Izquierdo ◽  
Atul Jain ◽  
Sarki Abdulkadir ◽  
Gary Schiltz

The chromenone core is an ubiquitous group in biologically active natural products and has been extensively used in organic synthesis. Fluorine-derived compounds, including those with a trifluoromethyl group (CF3), have shown enhanced biological activities in numerous pharmaceuticals compared with their non-fluorinated analogues. 2-Trifluoromethylchromenones can be readily functionalized at the 8- and 7-positions, providing chromenones cores of high structural complexity, which are excellent precursors for numerous trifluoromethyl heterocycles.


Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4341-4349
Author(s):  
Runtao Li ◽  
Runrun Li ◽  
Qiang Wei ◽  
Xin Wang ◽  
Zemei Ge

An efficient cascade synthesis of ethyl 3-amino-5-oxoisoxa­zolidine-4-carboxylate derivatives from diethyl 2-(ethoxymethyl­ene)malonate, different hydroxylamines and various amines is developed. This approach tolerates a wide range of amines affording highly functionalized isoxazolidine derivatives, which are expected to be important in organic synthesis and medicinal chemistry.


2020 ◽  
Author(s):  
Tobias Brandhofer ◽  
Volker Derdau ◽  
María Mendez ◽  
Christoph Pöverlein ◽  
Olga Garcia Mancheno

Abstract Visible light mediated late-stage functionalization is a rising field in synthetic and medicinal chemistry, allowing the fast and diversified modification of valuable, potentially therapeutic compounds such as peptides. However, there are relatively few mild methodologies for the C(sp3)-H functionalization of complex peptides. Herein, we report a visible light mediated photocatalytic protocol for the benzylic C-H modification of tyrosine and related C-H bonds. The embraced radical-cation/deprotonation strategy enables an incorporation of a wide range of valuable functional groups in high yields and chemoselectivity. The mild reaction conditions, site-selectivity and high functional group tolerance was highlighted by the functionalization of complex peptides, drugs and natural products, providing a promising synthetic platform in medicinal chemistry.


2015 ◽  
Vol 32 (4) ◽  
pp. 605-632 ◽  
Author(s):  
Michail Tsakos ◽  
Eva S. Schaffert ◽  
Lise L. Clement ◽  
Nikolaj L. Villadsen ◽  
Thomas B. Poulsen

In this review we investigate the use of complex ester fragment couplings within natural product total syntheses. Using examples from the literature up to 2014 we illustrate the state-of-the-art as well as the challenges within this area of organic synthesis.


2011 ◽  
Vol 83 (3) ◽  
pp. vi
Author(s):  
Leiv K. Sydnes

The 18th International Conference of Organic Synthesis (ICOS-18) was held in Bergen, Norway on 1-6 August 2010, under the auspices of IUPAC and with cosponsorship of the Norwegian Chemical Society and the Research Council of Norway. The structure of the meeting was in keeping with the tradition that has developed for the ICOS series of conferences, with a scientific backbone of lectures including the Thieme-IUPAC Prize Lecture, poster sessions, and exhibitions. Due to valuable help from members of the International Advisory Board, plenary and invited lectures were delivered by chemists from 22 different countries from all around the world. The talks covered most aspects of modern organic synthesis, from new delicate methodologies based on mechanistic understanding, via greatly improved synthesis technologies and exciting total syntheses, to the application of organic synthesis to meet challenges in bioorganic chemistry and the life sciences.There were two new features at this meeting. One was a section of five parallel sessions with short talks given mainly by young chemists from 22 countries. This event was expected to be a challenge to execute because, after all, we like to talk about chemistry without paying attention to the time, but thanks to the speakers’ exemplary discipline the chairs could be lenient in a firm fashion. Collectively, the short presentations showed that a wide range of new and brave ideas are investigated by the young colleagues, which indicate that organic synthesis is heading toward a bright future. The second addition was the Thieme-IUPAC Poster Prize, five in total, to the best posters presented at the conference as judged by an international committee of outstanding synthetic chemists.The papers published in this issue of Pure and Applied Chemistry (PAC) give a good cross-section of topics covered at ICOS-18. I am grateful to all colleagues for their interesting contributions, which are instrumental in helping IUPAC disseminate cutting-edge research to the enormous group of organic chemists that did not come to the conference. When you read the papers you will find reviews with excellent examples of natural-product syntheses, new synthetic methodologies, applications of organic synthesis in biological research, and development of new materials with exciting functional properties. But you will also come across interesting papers that are more like traditional publications found in journals other than PAC; the reason for this being that invitations were also extended to selected younger chemists to contribute papers based upon short talks (the scope of which was of course narrower than that of invited lectures), and they responded with enthusiasm. I am sure you will find interesting material there as well.ICOS-18 certainly nourished the organic synthetic chemists’ professional development through lectures, poster presentations, and discussions dealing with the cutting-edge advances in organic synthesis. There are many that are looking forward to the next meal, to be served when ICOS-19 opens in Melbourne, Australia, on 1 July 2012 (www.icos19.com).Leiv K. SydnesConference Editor


2021 ◽  
Vol 25 ◽  
Author(s):  
João Lucas Bruno Prates ◽  
Aline Renata Pavan ◽  
Jean Leandro dos Santos

: Nowadays, boron-containing compounds have gained researchers’ attention because of the wide versatility and applicability of this element in both organic and medicinal chemistry. Since its discovery, its use in medicinal chemistry was neglected due to its possible toxic effects. However, in the past years, boron-containing compounds did not show such effects, and some drugs have already been approved by the Food and Drug Administration to treat diseases, including cancer, infections, and inflammation. Several boron-containing compounds are used in organic and medicinal chemistry, either as a reagent or therapeutic agent. The chemical properties of this element make its use possible in organic synthesis as a reducing agent and catalyst, mainly in cross-coupling reactions. Among boron-containing compounds, boranes, azaborines, benzoxaborole, boronic acid, and boron derivatives are most commonly described. This review article discusses the main properties of boron-containing compounds, their preparation by organic synthesis, as well as their applications in organic synthesis and medicinal chemistry fields, developing new perspectives for further investigations.


Author(s):  
Yuriy Kuznetsov ◽  
Inna Levina ◽  
Igor Zavarzin

The monograph summarizes the information over the past 20 years on the currently widely used and promising methods for the synthesis of estra-1,3,5(10)-triene derivatives by modifying natural estrogens - estrone and estradiol. The main practical goals of modifying this class of steroids and achievements in the chemistry of steroidal antiestrogens, which are promising drugs for hormonal therapy, are considered. Special attention is paid to the stereochemical features of the reactions and the specific problems of modification of the steroid nucleus of estratrienes associated with the presence of an aromatic fragment in their structure. In addition, the data on the reactivity and stereochemical aspects of the transformations of 13-epiestratriene steroids were summarized. The monograph is intended for a wide range of specialists in the field of organic synthesis, organic, bioorganic, and medicinal chemistry.


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