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Author: Noah Frederick Fine Nathel Publisher: ISBN: Category : Languages : en Pages : 574
Book Description
Transition metal-catalyzed cross-coupling reactions are useful tools to assemble carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds. Traditionally, electrophilic halides and pseudohalides have been cross-coupled to their nucleophilic counterparts with palladium. Recently, however, the implementation of nickel as a catalyst for cross-coupling reactions has enabled the use of less reactive cross-coupling partners, such as carbamates, sulfamates, and amides. This dissertation describes the development of nickel-catalyzed cros-couplings of untraditional electrophiles to forge carbon-heteroatom (C-X) bonds. Additionally, the total syntheses of four indolactam alkaloids, indolactam V, pendolmycin, lyngbyatoxin A1 and teleocidin A-2, using both a key distortion-controlled indolyne reaction and palladium-catalyzed sp2-sp3 C-C bond construction, are described. Chapters one and two describe the development of nickel-catalyzed amination reactions of aryl electrophiles to form carbon-nitrogen (C-N) bonds. The amination reaction of aryl carbamates to form aryl amines is discussed. Subsequently, the development of green cross-couplings of aryl sulfamates and chlorides to similarly form aryl amines is reported. Chapter three introduces a means to accomplish a controlled cine substitution. This two-step process is comprised of a carbamate-directed ortho-lithiation/functionalization of an arene, followed by a nickel-catalyzed reductive deoxygenation of the directing group. This sequence provides a new strategy for synthesis and complements the more commonly employed ipso substitution in arene functionalization. Chapter four concerns the utility of amides as electrophilic cross-coupling partners. These traditionally unreactive moieties are activated by nickel and coupled to alcohols to form acyl C--O bonds. This study suggests that amides may serve as useful building blocks to construct C-X and C-C bonds. Chapter five describes the total syntheses of ( - )-indolactam V and its C7-substituted natural product derivatives, ( - )-pendolmycin, ( - )-lyngbyatoxin A1 and ( - )-teleocidin A-2. The C4-N linkage is constructed with a distortion-controlled indolyne functionalization. The total synthesis of ( - )-indolactam V provides a platform for the divergent syntheses of the other three natural products via a palladium-catalyzed cross-coupling to functionalize C7 and introduce a quaternary center.
Author: Noah Frederick Fine Nathel Publisher: ISBN: Category : Languages : en Pages : 574
Book Description
Transition metal-catalyzed cross-coupling reactions are useful tools to assemble carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds. Traditionally, electrophilic halides and pseudohalides have been cross-coupled to their nucleophilic counterparts with palladium. Recently, however, the implementation of nickel as a catalyst for cross-coupling reactions has enabled the use of less reactive cross-coupling partners, such as carbamates, sulfamates, and amides. This dissertation describes the development of nickel-catalyzed cros-couplings of untraditional electrophiles to forge carbon-heteroatom (C-X) bonds. Additionally, the total syntheses of four indolactam alkaloids, indolactam V, pendolmycin, lyngbyatoxin A1 and teleocidin A-2, using both a key distortion-controlled indolyne reaction and palladium-catalyzed sp2-sp3 C-C bond construction, are described. Chapters one and two describe the development of nickel-catalyzed amination reactions of aryl electrophiles to form carbon-nitrogen (C-N) bonds. The amination reaction of aryl carbamates to form aryl amines is discussed. Subsequently, the development of green cross-couplings of aryl sulfamates and chlorides to similarly form aryl amines is reported. Chapter three introduces a means to accomplish a controlled cine substitution. This two-step process is comprised of a carbamate-directed ortho-lithiation/functionalization of an arene, followed by a nickel-catalyzed reductive deoxygenation of the directing group. This sequence provides a new strategy for synthesis and complements the more commonly employed ipso substitution in arene functionalization. Chapter four concerns the utility of amides as electrophilic cross-coupling partners. These traditionally unreactive moieties are activated by nickel and coupled to alcohols to form acyl C--O bonds. This study suggests that amides may serve as useful building blocks to construct C-X and C-C bonds. Chapter five describes the total syntheses of ( - )-indolactam V and its C7-substituted natural product derivatives, ( - )-pendolmycin, ( - )-lyngbyatoxin A1 and ( - )-teleocidin A-2. The C4-N linkage is constructed with a distortion-controlled indolyne functionalization. The total synthesis of ( - )-indolactam V provides a platform for the divergent syntheses of the other three natural products via a palladium-catalyzed cross-coupling to functionalize C7 and introduce a quaternary center.
Author: Hans-Joachim Knoelker Publisher: Springer Science & Business Media ISBN: 3642255280 Category : Science Languages : en Pages : 268
Book Description
Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-
Author: Dewan S. Bhakuni Publisher: Springer Science & Business Media ISBN: 1402034849 Category : Science Languages : en Pages : 397
Book Description
Bioactive Marine Natural Products is the first book available that covers all aspects of bioactive marine natural products. It fills the void in the literature for bioactive marine natural products. The book covers various aspects of marine natural products and it is hoped that all the major classes of bioactive compounds are included. Different classes of marine organisms and the separation and isolation techniques are discussed. The chemistry and biology of marine toxins, peptides, alkaloids, nucleosides and prostanoids are discussed in detail. Biological, toxicological and clinical evaluations are also dealt with to ensure that the book may be adopted at any stage by any practicing organic chemist or biologist, working in academia or in R and D divisions of pharmaceutical companies. Each chapter in the book includes an abstract to highlight the major points discussed in the text and concluding remarks are given. References to books, monographs, review articles and original papers are provided at the end of each chapter.
Author: Akkattu T. Biju Publisher: John Wiley & Sons ISBN: 3527346465 Category : Science Languages : en Pages : 530
Book Description
A groundbreaking book to offer a a comprehensive account of important reactions involving arynes Modern Aryne Chemistry is the first book on the market to offer a conceptual framework to the reactions related to arynes. It also provides a systematic introduction to the cycloaddition reactions, insertion reactions and transition-metal-catalyzed transformations of arynes. The author, a noted expert on the topic, highlights a novel strategy for carbon-carbon and carbon-heteroatom bond construction using arynes. The book reveiws the recent use of aryne chemistry for the development of new multicomponent reactions. New advances in this area has shown rapid emergence of a new class of reactions classified under rearrangement reactions. The author also includes information on aryne methods that have been employed for the synthesis of several natural products. The simplicity and sophistication of the synthetic strategy using arynes can serve as a springboard for organic chemists to explore new possibilities and imagine applications of the concept of arynes. This important book: Presents a one-of-kind comprehensive guide to arynes reactions Offers a proven approach to the synthesis of natural product and polymers Reviews the most recent developments in the carbon-carbon and carbon-heteroatom bond-forming reactions involving arynes Written for organic, pharmaceutical, medicinal, natural products, and catalytic Chemists, Modern Aryne Chemistry offers a comprehensive review of the fundamentals of reactions related to arynes and the most recent developments in the field.
Author: Majid M. Heravi Publisher: Elsevier ISBN: 0128242582 Category : Science Languages : en Pages : 404
Book Description
Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids includes comprehensive coverage of name reactions in the synthesis of alkaloids. This book highlights the synthesis of various alkaloids using special name reactions including the Diels-Alder, Friedel-Crafts, Heck, Mannich, Pauson-Khand, Pictet-Spengler, Sonogashira and Suzuki reactions. In this book, some selected name reactions in the total synthesis of alkaloids are covered, as they can be used as the key step/steps in the synthesis of different alkaloids exhibiting various biological activities. All chapters include an introduction, history and mechanism of the name reaction, and present the origin of the natural product and its known biological activities. The pathway to total synthesis is visually illustrated, and the focus is on the step in which a name reaction is applied. Chemists working in the area of synthetic organic chemistry will find this reference useful, as well as those working to develop novel methodologies for the synthesis of natural products in both academia and industry. This book is also beneficial to biologists, pharmacists and botanists. Includes an introduction of alkaloids, their origins and biological properties Features the applications of special name reactions as the key step in the total synthesis of featured alkaloids Covers the pathway for the synthesis of alkaloids from commercially available or easily accessible starting materials by using at least one name reaction to achieve the desired target products
Author: Neil Garg Publisher: ISBN: 9780692860540 Category : Languages : en Pages : 30
Book Description
This coloring book brings to life the magic and impact of organic chemistry for children and adults alike. With more than 25 pages to color, kids will have fun and even learn some science too! The molecules featured in this book include sucrose, aspirin, caffeine, cellulose, proteins, and many more. This educational coloring book was created by two children, with the help of their father, a UCLA Chemistry Professor. "This coloring book brings the unbridled curiosity of a young mind together with the wonders of our molecular world in ways that will surely inspire discovery, fun, and perhaps a lifelong appreciation of the ubiquity and impact of chemistry" -Professor Paul Wender (Stanford University)
Author: A. Douglas Kinghorn Publisher: Springer ISBN: 3319331728 Category : Science Languages : en Pages : 258
Book Description
The first contribution reviews the phytochemical, chemical, and biological literature on members of the ingenane class of diterpenoids from their first isolation in 1968 through 2015, highlighting unresolved issues both common to phorboids and specific to ingenol derivatives. The biogenesis of ingenol is discussed in the light of the Jakupovic proposal of a dissection between the formation of the macrocyclic Euphorbia diterpenoids and the phorboids, and the clinical development of ingenol mebutate is chronicled in the light of its “reverse-pharmacology” focus. The second contribution offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. It addresses the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; the secondary metabolites as well as their sources of isolation; and finally the biological activity.
Author: Stefan Bräse Publisher: John Wiley & Sons ISBN: 0470682523 Category : Science Languages : en Pages : 536
Book Description
Most current state-of-the-art overview of this important class of compounds, encompassing many new and emerging applications The number of articles on organic azides continues to increase tremendously; on average, there are more than 1000 new publications a year Covers basic chemistry as well as state-of-the-art applications in life science and materials science World-ranked authors describe their own research in the wider context of azide chemistry Includes a chapter on safe synthesis and handling (azides can decompose explosively)
Author: Joffrey Vrijdag Publisher: ISBN: 9781536176957 Category : Science Languages : en Pages : 268
Book Description
"Cross-Coupling Reactions: An Overview opens with an overview of the fundamentals and applications of the young and fast developing area of transition metal catalyzed/mediated oxidative (dehydrogenative) C-H/C-H coupling reactions between two (hetero)arenes. Continuing, the authors highlight the recent advances regarding the ligand supported transition metal-catalyzed domino (cascade) or one-pot syntheses of various heterocycles involving cross-coupling reactions. The recent advances in Cu catalyzed tandem reactions for heterocycle synthesis are also addressed. Cu metal chemistry has garnered attention as a potential alternative to precious transition metals, being cheaper, more sustainable and more easily available. A comprehensive account of research on green chemical routes is provided, involving various palladium metal-based catalysts utilized in facilitating cross-coupling reaction in aqueous media. Reported decarboxylative cross-coupling reactions are discussed along with suitable examples, focusing on their mechanism of action"--
Author: Noah Frederick Fine Nathel
Author: Noah Frederick Fine Nathel
Author: E.J. Corey
Author: Hans-Joachim Knoelker
Author: Dewan S. Bhakuni
Author: Akkattu T. Biju
Author: Majid M. Heravi
Author: Neil Garg
Author: A. Douglas Kinghorn
Author: Stefan Bräse
Author: Joffrey Vrijdag