Cascade Ring Expansion Reactions for Synthesis of Medium-sized Rings and Macrocycles PDF Download

Author: Illya Zalessky
Publisher:
ISBN:
Category :
Languages : en
Pages : 0

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This note is part of Quality testing.

Author: Manfred Hesse
Publisher:
ISBN:
Category : Science
Languages : en
Pages : 256

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Author: Christopher F. Stratton
Publisher:
ISBN:
Category :
Languages : en
Pages : 548

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Macrocycles are large ring structures found in a wide variety of bioactive natural products. The macrocyclic constraint is a key structural element that orients functional groups in three-dimensional space for presentation to binding sites on biological targets. This conformational restriction has also been associated with increased binding affinity and oral bioavailability compared to corresponding linear structures. Accordingly, macrocycles are attractive targets in the diversity-oriented synthesis of natural product-based libraries for probe and drug discovery screening. However, macrocycles have been severely underutilized in this regard as efficient access to diverse collections of macrocyclic scaffolds has been hampered by challenges associated with traditional macrocyclization reactions. To address this problem, we have developed a concise, modular approach to the diversity-oriented synthesis of macrolactones and macrolactams using the oxidative cleavage of a bridging bond in polycyclic enol ethers and enamines. These substrates are assembled in only four or five synthetic steps and undergo ring expansion to afford highly functionalized macrocycles bearing handles for further diversification. In contrast to macrocyclization reactions of corresponding linear seco -acids, the ring expansion reactions are efficient and insensitive to ring size and stereochemistry, overcoming key limitations of conventional approaches to systematic macrocycle synthesis. Cheminformatic analyses of our macrocycle scaffolds indicate that these molecules access underrepresented regions of chemical space that overlap with natural products, including known macrolactones and macrolactams, and are complementary to those addressed by existing synthetic drugs and drug-like libraries. Efficient access to diverse collections of macrocycles is hoped to facilitate the continued evaluation of this important class of molecules in addressing challenging biological targets.

Author: Andrea Basso
Publisher: Frontiers Media SA
ISBN: 2889457885
Category :
Languages : en
Pages : 150

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Has the concept of Diversity Oriented Synthesis remained unchanged over these two decades, or do we observe improvements or deviations from the original guidelines drawn by the pioneers? The aim of this Research Topic is to collect contributions on the state-of-the-art and progress of Diversity Oriented Synthesis, and to foresee its shape in the next decade.

Author: Vithalanand R. Kulkarni
Publisher:
ISBN:
Category : Phosphonates
Languages : en
Pages : 500

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Author: Teresa M. V. D. Pinho e Melo
Publisher: John Wiley & Sons
ISBN: 3527832017
Category : Science
Languages : en
Pages : 564

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Heterocycles A must-read handbook on heterocycle chemistry with a focus on sustainability Heterocycles feature prominently in our daily life—they are essential for pharmaceuticals, agrochemicals, and fine chemicals. More, numerous natural, bioactive products contain heterocyclic compounds. As a result, heterocyclic chemistry continues to be one of the most important areas of study in organic chemistry. Heterocycles provides an important reference on a wide range of topics relating to heterocyclic chemistry, with a heavy emphasis on sustainable methods and greener syntheses. The book describes state-of-the-art synthetic methods, such as photochemical reactions, dearomatization reactions, organocatalysis, transition metal catalysis, and biocatalysis. It also covers: Sustainable methods, like flow chemistry, mechanochemistry, and multicomponent synthesis Strategies for the synthesis of heterocyclic macrocycles and medium-sized rings Characterization of heterocyclic compounds Heterocycles is a useful reference for organic chemists, natural products chemists, catalytic chemists, and medicinal chemists in academia and industry.

Author: José Pérez Sestelo
Publisher: MDPI
ISBN: 3039435671
Category : Science
Languages : en
Pages : 234

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In this Special Issue, recent advances in cross-coupling reactions are presented in the form of original research articles, reviews, and short communications. These contributions cover different topics in this area, including novel coupling reactions, reaction conditions, synthetic alternatives, metal ligands, and applications for new pharmaceutical compounds and organic materials. In particular, the reviews deal with methodologies such as the synthesis of diarylketones through palladium catalysis and the most relevant examples of Suzuki–Miyaura and Buchwald–Hartwig coupling reactions in the synthesis of bioactive compounds. The synthetic utility of cross-coupling reactions for the synthesis of medium-size rings and the utility of Stille and Suzuki coupling reactions for the synthesis of new molecular machines based on sterically hindered anthracenyl trypticenyl units are also summarized. The original research articles present the synthesis of 2-alkynylpyrrols by inverse Sonogashira coupling and the synthesis of indoles under oxidative dearomative cross-dehydrogenative conditions. The efficient combination of iridium-catalyzed C–H borylation of aryl halides with the Sonogashira coupling and a sequential iridium-catalyzed borylation of NH-free pyrroles followed by a Suzuki–Miyaura reaction are included. The synthesis of aryl propionic acids, a common structural motif in medicinal chemistry, and the synthesis of new organic dyes are also covered.

Author: J. A. Semlyen
Publisher: Springer Science & Business Media
ISBN: 0412830906
Category : Science
Languages : en
Pages : 804

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Book Description
Cyclic Polymers (Second Edition) reviews the many recent advances in this rapidly expanding subject since the publication of the first edition in 1986. The preparation, characterisation, properties and applications of a wide range of organic and inorganic cyclic oligomers and polymers are described in detail, together with many examples of catenanes and rotaxanes. The importance of large cyclics in biological chemistry and molecular biology is emphasised by a wide coverage of circular DNA, cyclic peptides and cyclic oligosaccharides and polysaccharides. Experimental techniques and theoretical aspects of cyclic polymers are included, as well as examples of their uses such as ring opening polymerisation reactions to give commercially important materials. This book covers a wide range of topics which should be of interest to many scientific research workers (for example, in polymer science, chemistry and molecular biology), as well as providing a reference text for undergraduate and graduate students.

Author: Jonathan L Sessler
Publisher: Royal Society of Chemistry
ISBN: 1847552471
Category : Science
Languages : en
Pages : 431

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Book Description
Anion recognition plays a critical role in a range of biological processes, and a variety of receptors and carriers can be found throughout the natural world. Chemists working in the area of supramolecular chemistry have created a range of anion receptors, drawing inspiration from nature as well as their own inventive processes. This book traces the origins of anion recognition chemistry as a unique sub-field in supramolecular chemistry while illustrating the basic approaches currently being used to effect receptor design. The combination of biological overview and summary of current synthetic approaches provides a coverage that is both comprehensive and comprehensible. First, the authors detail the key design motifs that have been used to generate synthetic receptors and which are likely to provide the basis for further developments. They also highlight briefly some of the features that are present in naturally occurring anion recognition and transport systems and summarise the applications of anion recognition chemistry. Providing as it does a detailed review for practitioners in the field and a concise introduction to the topic for newcomers, Anion Receptor Chemistry reflects the current state of the art. Fully referenced and illustrated in colour, it is a welcome addition to the literature.

Author: Jeremy I Levin
Publisher: Royal Society of Chemistry
ISBN: 1849737010
Category : Medical
Languages : en
Pages : 526

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Book Description
This series provides a comprehensive resource for postgraduate students and for scientists in academia or industry wanting to learn topics outside their own areas of expertise.