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Author : Michael N. Greco
Publisher :
ISBN 13 :
Total Pages : 354 pages
Book Rating : 4.:/5 (128 download)
Download or read book The Total Synthesis of Two Structurally Unique Indole Alkaloids written by Michael N. Greco and published by . This book was released on 1983 with total page 354 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Junpei Matsuoka
Publisher : Springer Nature
ISBN 13 : 9811586527
Total Pages : 91 pages
Book Rating : 4.8/5 (115 download)
Download or read book Total Synthesis of Indole Alkaloids written by Junpei Matsuoka and published by Springer Nature. This book was released on 2020-09-18 with total page 91 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. The book first describes the total and formal synthesis of dictyodendrins A–F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds.
Author : W. I. Taylor
Publisher : Elsevier
ISBN 13 : 1483221741
Total Pages : 162 pages
Book Rating : 4.4/5 (832 download)
Download or read book Indole Alkaloids written by W. I. Taylor and published by Elsevier. This book was released on 2013-09-17 with total page 162 pages. Available in PDF, EPUB and Kindle. Book excerpt: A Course in Organic Chemistry Advanced Section, Volume 27: Indole Alkaloids: An Introduction to the Enamine Chemistry of Natural Products describes the chemistry of selected alkaloids that contain indolic or closely related nuclei. Some five hundred of these compounds have been obtained from about three hundred plants mostly of the family Apocynaceae. This book is composed of 12 chapters that specifically cover the chemistry of the complex indoles. The introductory chapters deal with the origin, isolation, characterization, basic chemistry, and simple derivatives of indole alkaloids. The remaining chapters examine the biogenesis, basic chemistry, stereochemistry, and structure of selected complex alkaloids of various origins. These chapters include tetrahydro-?-carboline, strychnos, iboga, picralima, and eburnamine alkaloids, cinchonamine, quinamine, and ajmaline-sarpagine bases. This text is of great value to organic chemists and researchers.
Author : Maliha Uroos
Publisher : Elsevier
ISBN 13 : 0323972489
Total Pages : 236 pages
Book Rating : 4.3/5 (239 download)
Download or read book Indole Alkaloids written by Maliha Uroos and published by Elsevier. This book was released on 2022-01-30 with total page 236 pages. Available in PDF, EPUB and Kindle. Book excerpt: Indole Alkaloids: Spirooxindole details the multistep synthesis of natural products using schematic diagrams, providing a quick-and-easy way to review and understand new and novel synthetic strategies to construct structural frameworks of natural products. As a volume in the Visual Guides to Natural Product Synthesis series, this book presents the schematic total syntheses of natural products containing a "spirooxindole core structure. It covers spirooxindole molecules through visual diagrams, highlighting key steps involved in total, formal and semi-syntheses. Sections cover Brevianamide A and B, Citrinadin A and B, Coerulescine and Horsfiline, Elacomine and Isoelacomine, Gelsemine, Paraherquamide A and B, Rynchophylline, Isorynchophylline, and more. Visual layouts provide quick-and- easy access to developed synthetic routes towards the targeted spirooxindoles. - Outlines synthetic strategies for natural products bearing a spirooxindole core structure - Includes schematic diagrams of multistep synthetic routes, highlighting key steps along the way - Describes all routes for the formal synthesis, semi-synthesis and total synthesis of spirooxindole alkaloids
Author : Majid M. Heravi
Publisher : Elsevier
ISBN 13 : 0128242582
Total Pages : 404 pages
Book Rating : 4.1/5 (282 download)
Download or read book Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids written by Majid M. Heravi and published by Elsevier. This book was released on 2021-06-12 with total page 404 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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 : Kengadarane Anebouselvy
Publisher : Royal Society of Chemistry
ISBN 13 : 1782620907
Total Pages : 220 pages
Book Rating : 4.7/5 (826 download)
Download or read book Dienamine Catalysis for Organic Synthesis written by Kengadarane Anebouselvy and published by Royal Society of Chemistry. This book was released on 2018-03-02 with total page 220 pages. Available in PDF, EPUB and Kindle. Book excerpt: In the last decade a new era in asymmetric catalysis has been realised by the discovery of L-proline induced chiral enamines from carbonyls. Inspired by this, researchers have developed many other primary catalytic species in situ, more recently secondary catalytic species such as aminals have been identified for use in asymmetric synthesis. High-yielding asymmetric synthesis of bioactive and natural products through mild catalysis is an efficient approach in reaction engineering. In the early days, synthetic chemists mainly focused on the synthesis of complex molecules, with less attention on the reaction efficiency and eco-friendly conditions. Recent investigations have been directed towards the development of atom economy, eco-friendly and enantioselective synthesis for more targeted and efficient synthesis. Building on the momentum of this rapidly expanding research area, Dienamine catalysis for organic synthesis will provide a comprehensive introduction, from the preformed species, in situ generation and onto their applications in the synthesis of bioactive molecules and natural products.
Author : Eduardo Valentin Mercado-Marin
Publisher :
ISBN 13 :
Total Pages : 356 pages
Book Rating : 4.:/5 (957 download)
Download or read book A Unified Approach Toward the Total Syntheses of Prenylated Indole Alkaloid Natural Products written by Eduardo Valentin Mercado-Marin and published by . This book was released on 2016 with total page 356 pages. Available in PDF, EPUB and Kindle. Book excerpt: Abstract A Unified Approach Toward the Total Syntheses of Prenylated Indole Alkaloid Natural Products by Eduardo Valentin Mercado-Marin Doctor of Philosophy in Chemistry University of California, Berkeley Professor Richmond Sarpong, Chair This dissertation describes our approach toward a unifying synthesis of prenylated indole alkaloid natural products. Chapter 1 is an introduction and provides background to this class of natural products, focusing primarily on the isolation, biological activity, biosynthetic, and previous synthetic work of these natural products. This section also includes a discussion of synthetic approaches to the common bicyclo[2.2.2]diazaoctane core embodied in many of these natural products, which sets the stage for our entry into these molecules by a unifying route. Chapter 2 describes our entry into this class of natural products focused primarily on our synthetic and biosynthetic work toward natural products lacking the bicyclo[2.2.2]diazaoctane core. In particular, we discuss the first chemical syntheses of the prenylated indole alkaloids citrinalin B and cyclopiamine B. Along with unambiguously establishing the structures of these natural products, in collaboration with the Berlinck group, we provide evidence for the existence of a common bicyclo[2.2.2]diazaoctane containing precursor as an intermediate to natural products that lack this structural feature. Lastly, Chapter 3 describes our unified strategy for the synthesis of prenylated indole alkaloid natural products, capitalizing on our results described in Chapter 2. This unifying strategy has resulted in the syntheses of stephacidin A and 17-hydroxy-citrinalin B. Key to the success of this approach in accessing congeners containing and lacking the bicyclo[2.2.2]diazaoctane core was a complexity building isocyanate capture to forge the bicyclo[2.2.2]diazaoctane core from a common all fused precursor.
Author : Connor L. Martin
Publisher :
ISBN 13 : 9781124400716
Total Pages : 328 pages
Book Rating : 4.4/5 (7 download)
Download or read book First Total Synthesis of (+/- )- and ( - )-actinophyllic Acid and First Enantioselective Total Synthesis of Condylocarpine-type Alkaloids written by Connor L. Martin and published by . This book was released on 2011 with total page 328 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter 1. The unique indole alkaloid ( - )-actinophyllic acid (1) is introduced. Its biological activity, structural relationship to other indole alkaloids, and potential biosynthesis are discussed. Our plan for synthesizing ( - )-actinophyllic acid with the use of the aza-Cope/Mannich reaction as a key step is described in detail. Chapter 2. The first-generation total synthesis of (±)-actinophyllic acid (rac-1) is described. The central step in this synthesis is the aza-Cope/Mannich reaction, which constructs the core of the previously unknown hexacyclic ring system of actinophyllic acid from a much simpler tetracyclic precursor. The hexahydro-1,5-methano-1H-azocino[4,3-b]indole ketone rac-121 is assembled from o-nitrophenylacetic acid in four steps, with oxidative cyclization of the dienolate derivative of tricyclic precursor rac-119 being the pivotal step. In the most concise route, rac-121 is elaborated to allylic alcohol rac-130, which is transformed to pentacyclic ester rac-134 by a one-pot global deprotection-aza-Cope/Mannich-Fisher esterification sequence. In two additional steps, this intermediate is advanced to (±)-actinophyllic acid. Chapter 3. The second-generation total syntheses of (±)-actinophyllic acid (rac-1) and ( - )-actinophyllic acid (1) are described. The first-generation synthesis is streamlined by elaborating ketone rac-121 to B-hydroxyester intermediate rac-141, which is directly transformed to (±)-actinophyllic acid upon exposure to HCl and paraformaldehyde. This concise synthesis of (±)-actinophyllic acid is realized in 22% overall yield from commercially available di-tert-butyl malonate and o-nitrophenylacetic acid by a sequence that proceeds by way of only six isolated intermediates. The first enantioselective total synthesis of ( - )-actinophyllic acid (1) is accomplished by this direct sequence from tricyclic keto malonate (S)-119. Catalytic enantioselective reduction of enone 163 is the key step in the preparation of intermediate (S)-119 from the commercially available Boc-amino acid 161. Chapter 4. The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are described. (+)-Condylocarpine (174a), (+)-isocondylocarpine (174b), and (+)-tubotaiwine (217) are prepared in high enantiomeric purity (>99% ee) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one (1S,5R)-121 by way of five or six isolated intermediates.
Author : Hans-Joachim Knoelker
Publisher : Springer Science & Business Media
ISBN 13 : 3642255280
Total Pages : 268 pages
Book Rating : 4.6/5 (422 download)
Download or read book Alkaloid Synthesis written by Hans-Joachim Knoelker and published by Springer Science & Business Media. This book was released on 2012-01-13 with total page 268 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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 : Robert A. Farr
Publisher :
ISBN 13 :
Total Pages : 298 pages
Book Rating : 4.:/5 (857 download)
Download or read book The Total Synthesis of 16, 17-dihydrosecodine and Related Indole Alkaloids written by Robert A. Farr and published by . This book was released on 1981 with total page 298 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Gordon W. Gribble
Publisher : John Wiley & Sons
ISBN 13 : 0470512180
Total Pages : 704 pages
Book Rating : 4.4/5 (75 download)
Download or read book Indole Ring Synthesis written by Gordon W. Gribble and published by John Wiley & Sons. This book was released on 2016-08-08 with total page 704 pages. Available in PDF, EPUB and Kindle. Book excerpt: Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments. The indole ring continues to be discovered in natural products and to be employed in man-made pharmaceuticals and other materials. Given the enormous resurgence in indole ring synthesis over the past decade — highlighted by the power of transition metal catalysis — this authoritative guide addresses the need for a comprehensive presentation of the myriad of methods for constructing the indole ring, from the ancient to the modern, and from the obscure to the well-known. Following presentation of the classic indole ring syntheses and many newer methods, coverage continues with indole ring syntheses via pyrroles, indolines, oxindoles, isatins, radical and photochemical reactions, aryne cycloadditions. This extensive volume concludes with the modern transition metal–catalyzed indole ring syntheses that utilize copper, palladium, rhodium, gold, ruthenium, platinum, and other metals to fashion the indole ring Indole Ring Synthesis is a comprehensive, authoritative and up-to-date guide to the synthesis of this important heterocycle for organic chemists, pharmaceutical researchers and those interested in the chemistry of natural products.
Author : Lucas Morrill
Publisher :
ISBN 13 :
Total Pages : 395 pages
Book Rating : 4.:/5 (11 download)
Download or read book Total Syntheses of Indole Alkaloids and Determination of the Electrophilicity of Benzyne and Related Intermediates written by Lucas Morrill and published by . This book was released on 2019 with total page 395 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation encompasses several projects pertaining to natural product total synthesis, reaction methodology development, and kinetic studies. The total synthesis of natural products continues to be a fruitful area of research in organic chemistry. The successful completion of a total synthesis endeavor not only affirms ambitious route designs, but can also allow access to significant amounts of biologically-active compounds. Given that natural product structures inspire the development of new agrochemicals and pharmaceuticals, their syntheses are a worthwhile endeavor. Also, the development of new reaction methodologies and the understanding of fundamental reactivities of many intermediates remain important areas of research. Chapter One offers a current perspective on the field of natural product total synthesis. Alhough historically viewed as a highly competitive field, several recent examples show the growing spirit of collaboration in total synthesis. By forming alliances with chemists in other fields, industries, or laboratories, total synthesis chemists have made many breakthroughs that would arguably not be possible if working independently. Chapters Two and Three describe our laboratory's total syntheses of several bioactive akuammiline alkaloids, including strictamine, 2(S)-cathafoline, akuammiline, -akuammigine, and 10-demethoxynorvincorine. Our strategic approach to the natural products focused on the use of a modern variant of a classic reaction, the Fischer indolization reaction, to install several rings and the common quaternary center found in each target. This strategy allowed for the first total syntheses of akuammilines bearing the methanoquinolizidine core and those that also bear vicinal quaternary centers. In addition, rearrangements of the methanoquinolizidine core were developed that allowed us to access pyrrolidinoindoline-containing akuammilines. Chapter Four describes a series of kinetic studies used to determine the electrophilicity parameter of benzyne and related aryne intermediates. Arynes are a family of strained intermediates whose existence has been postulated for over 100 years. Recent advances have confirmed their existence and proven their synthetic utility. An advanced knowledge of their reactivity thus far has remained elusive. Our laboratory employed the diffusion clock method to measure the rates of reaction between several arynes and a variety of different nucleophilic reaction partners. The result allowed for the first quantification of the electrophilicity of these strained intermediates and should influence synthetic planning in the future. Chapter Five includes a study in the development of reaction methodology. Utilizing a variant of the Fischer Indolization reaction, our laboratory discovered a general method for making aza-indoline structures. This methodology was applied in the synthesis of derivatives of akuammiline alkaloids and Alzheimer's therapeutic molecules. In addition, a predictive computational model of reactivity was derived.
Author : K. C. Nicolaou
Publisher : John Wiley & Sons
ISBN 13 : 3527292314
Total Pages : 826 pages
Book Rating : 4.5/5 (272 download)
Download or read book Classics in Total Synthesis written by K. C. Nicolaou and published by John Wiley & Sons. This book was released on 1996-04-11 with total page 826 pages. Available in PDF, EPUB and Kindle. Book excerpt: K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry This book is a must for every synthetic chemist. With didactic skill and clarity, K. C. Nicolaou and E. Sorensen present the most remarkable and ingenious total syntheses from outstanding synthetic organic chemists. To make the complex strategies more accessible, especially to the novice, each total synthesis is analyzed retrosynthetically. The authors then carefully explain each synthetic step and give hints on alternative methods and potential pitfalls. Numerous references to useful reviews and the original literature make this book an indispensable source of further information. Special emphasis is placed on the skillful use of graphics and schemes: Retrosynthetic analyses, reaction sequences, and stereochemically crucial steps are presented in boxed sections within the text. For easy reference, key intermediates are also shown in the margins. Graduate students and researchers alike will find this book a gold mine of useful information essential for their daily work. Every synthetic organic chemist will want to have a copy on his or her desk.
Author : William I. Taylor
Publisher : Pergamon
ISBN 13 :
Total Pages : 170 pages
Book Rating : 4.:/5 (44 download)
Download or read book Indole Alkaloids written by William I. Taylor and published by Pergamon. This book was released on 1966 with total page 170 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Paul Joseph Reider
Publisher :
ISBN 13 :
Total Pages : 248 pages
Book Rating : 4.:/5 (414 download)
Download or read book The Total Synthesis of Indole Alkaloids written by Paul Joseph Reider and published by . This book was released on 1978 with total page 248 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Jun Ma
Publisher :
ISBN 13 :
Total Pages : 464 pages
Book Rating : 4.:/5 (123 download)
Download or read book Part I. General Approach to the Total Synthesis of 9-methoxy Substituted Indole Alkaloids written by Jun Ma and published by . This book was released on 2006 with total page 464 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Reuben Murray White
Publisher :
ISBN 13 :
Total Pages : 258 pages
Book Rating : 4.:/5 (18 download)
Download or read book Synthesis of Indole Alkaloids written by Reuben Murray White and published by . This book was released on 2019 with total page 258 pages. Available in PDF, EPUB and Kindle. Book excerpt:
