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Synthetic Strategies Toward Aconitine Type And Hetisine Type Diterpenoid Alkaloids
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Book Synopsis Synthetic Strategies Toward Aconitine-type and Hetisine-type Diterpenoid Alkaloids by : Jason Jon Pflueger
Download or read book Synthetic Strategies Toward Aconitine-type and Hetisine-type Diterpenoid Alkaloids written by Jason Jon Pflueger and published by . This book was released on 2016 with total page 159 pages. Available in PDF, EPUB and Kindle. Book excerpt: Diterpenoid alkaloid natural products, isolated from plants in the Aconitum, Delphinium, Consolida, and Spiraea genera, possess complex, caged, highly oxygenated skeletons and display potent biological activities through interactions with voltage-gated ion channels. Several of these alkaloids are currently used clinically for the treatment of arrhythmia, while others act as incredibly potent neurotoxins. Until recently, there were very few successful total syntheses of any diterpenoid alkaloid natural products, a testament to the structural complexity of these molecules. We explored synthetic strategies targeting two major types of these natural products: the aconitine-type C19-diterpenoid alkaloids and the hetisine-type C20-diterpenoid alkaloids. Initial work explored Diels-Alder cycloadditions with maleic anhydride-derived dienophiles toward the eventual construction of aconitine-type diterpenoid alkaloids. We examined the selective ring-opening of these adducts with a variety of nucleophiles and utilized an ester-stabilized benzylic nucleophile to achieve C-C bond formation with complete positional selectivity. This product was rapidly elaborated to a vinyl lactone intermediate, which following amine addition and oxidation underwent a high-yielding, diastereoselective methylation reaction to install the challenging C18 carbon atom. Synthesis of the hetisine-type diterpenoid alkaloid cossonidine built off of previous work performed in the Sarpong lab. Reexamining the previously-developed route, we optimized several steps and implemented new reactions to increase the yield and reproducibility of the chemistry and reduce the overall step count. Subsequent functional group transformations involving deprotection and inversion of the C1 hydroxyl group and installation of the allylic alcohol moiety completed the first total synthesis of cossonidine. Recognizing the connections between the various diterpenoid alkaloid types, we explored ways to convert the vinyl lactone intermediate developed in our studies toward aconitine-type natural products into the hetisine-type skeleton of cossonidine. Following the introduction of an iodine atom on the aromatic ring, magnesium-halogen exchange leads to an intramolecular cyclization reaction to forge the central 6-7-6 tricycle with carbonyl groups at all three nitrogen-bearing carbon atoms following oxidation. Efforts to install the C18 methyl group and accomplish a triple reductive amination cascade to complete this second-generation total synthesis are ongoing.
Book Synopsis A Ring Expansion Strategy Toward the Synthesis of Hetisine-Type C20-Diterpenoid Alkaloids by : Jessica Kristine Kisunzu
Download or read book A Ring Expansion Strategy Toward the Synthesis of Hetisine-Type C20-Diterpenoid Alkaloids written by Jessica Kristine Kisunzu and published by . This book was released on 2014 with total page 135 pages. Available in PDF, EPUB and Kindle. Book excerpt: A benzyne insertion ring expansion strategy toward the synthesis of hetisine-type C20-diterpenoid alkaloids has been developed. The first chapter of this manuscript presents an introduction to C20-diterpenoid alkaloids and previous synthetic work toward selected target core structures. The second and third chapters outline our ring expansion strategy for the synthesis of the core of the natural product cossonidine and efforts to complete its total synthesis. An overview of the structural and biological properties of C20-diterpenoid alkaloids is provided, as well as a survey of the synthetic studies that have been carried out thus far toward natural products containing the hetidine and hetisine-type framework. The two existing syntheses of a hetisine-type diterpenoid alkaloid are also described. This review outlines some of the salient structural challenges associated with the synthesis of these compounds, as well as the strategies applied to their construction. An approach involving a ring expansion was developed to access a tricyclic motif conserved in the hetidine and hetisine frameworks. The acyl-alkylation of aryne intermediates by insertion into C-C sigma bonds was applied to several [beta]-ketoesters and aryne precursors to investigate the efficacy of this transformation on complex systems. Three tricyclic intermediates were synthesized that contain functional handles at the appropriate positions for C-N bond formation to construct the hetisine core. With a sequence in place to arrive as several desired tricyclic intermediates, they were then employed to investigate C-N bond formation. A range of conditions was explored, and the desired azabicycle was accessed in 3 steps from the tricyclic scaffold. The requisite [2.2.2] bicycle was then formed in 2 steps to complete the hetisine core. Finally, the synthetic sequence was modified in order to introduce a methyl group necessary for completion of the natural product target. This methylation pathway has been successful in providing the full hetisine core en route to the synthesis of the natural product cossonidine.
Book Synopsis Development of a Unified Strategy to the C18-, C19-, and C20-Diterpenoid Alkaloids by : Christopher James Marth
Download or read book Development of a Unified Strategy to the C18-, C19-, and C20-Diterpenoid Alkaloids written by Christopher James Marth and published by . This book was released on 2015 with total page 337 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter 1 of this dissertation lays the foundation for understanding the role diterpenoid alkaloid natural products could play in the development of novel pharmaceuticals and probes for chemical biology applications. The chapter describes ethnomedical uses of Aconitum plants, the bioactivities of select diterpenoid alkaloids, and successful total syntheses of the diterpenoid alkaloids. Chapter 2 details our 'family-oriented' strategy for developing a unified route to the C18-, C19-, and C20-diterpenoid alkaloids. By identifying the common fragments comprising the structural complexity of the diterpenoid alkaloids, we have been able to expedite our retrosynthetic analysis centered on a divergent strategy towards accessing members in each of the families. Chapter 3 describes our efforts at employing the AE ring fragment for the synthesis of the diterpenoid alkaloids. Key to this strategy is the use of a meta-[pi]-arene photocycloaddition reaction for directly constructing the [3.2.1] bicycle of the C18- and C19-diterpenoid alkaloids. Efforts toward accomplishing this objective are detailed herein along with an improved methylenation sequence of the hydrindanone core, a single-step lactone to lactam chemical transformation, and aryl addition attempts to AE bicycle containing substrates. Chapter 4 focuses on our efforts at employing the AEF tricycle in the synthesis of the C18- and C19-diterpenoid alkaloids using cycloaddition strategies. Various meta-[pi]-arene photocycloaddition precursors were synthesized, and a successful substrate was identified. The major differences between the successful and unsuccessful substrates are described in the chapter, as well as efforts towards employing alternative cycloaddition strategies for forging the targeted [3.2.1] bicycle. Chapter 5 details our unified strategy to the diterpenoid alkaloids. Described in this chapter are the rearrangement of the C20-denudatine type [2.2.2] bicycle to the [3.2.1] bicycle of the C18 and C19 natural products, the use of the rearrangement in the synthesis of liljestrandinine (C19), and current work towards the synthesis of weisaconitine D (C18).
Book Synopsis Stereoselective Synthesis of Drugs and Natural Products by : Vasyl Andrushko
Download or read book Stereoselective Synthesis of Drugs and Natural Products written by Vasyl Andrushko and published by John Wiley & Sons. This book was released on 2013-08-16 with total page 1836 pages. Available in PDF, EPUB and Kindle. Book excerpt: Brings together the best tested and proven stereoselective synthetic methods Both the chemical and pharmaceutical industries are increasingly dependent on stereoselective synthetic methods and strategies for the generation of new chiral drugs and natural products that offer specific 3-D structures. With the publication of Stereoselective Synthesis of Drugs and Natural Products, researchers can turn to this comprehensive two-volume work to guide them through all the core methods for the synthesis of chiral drugs and natural products. Stereoselective Synthesis of Drugs and Natural Products features contributions from an international team of synthetic chemists and pharmaceutical and natural product researchers. These authors have reviewed the tremendous body of literature in the field in order to compile a set of reliable, tested, and proven methods alongside step-by-step guidance. This practical resource not only explores synthetic methodology, but also reaction mechanisms and applications in medicinal chemistry and drug discovery. The publication begins with an introductory chapter covering general principles and methodologies, nomenclature, and strategies of stereoselective synthesis. Next, it is divided into three parts: Part One: General Methods and Strategies Part Two: Stereoselective Synthesis by Bond Formation including C-C bond formation C-H bond formation C-O bond formation C-N bond formation Other C-heteroatom formation and other bond formation Part Three: Methods of Analysis and Chiral Separation References in every chapter serve as a gateway to the literature in the field. With this publication as their guide, chemists involved in the stereoselective synthesis of drugs and natural products now have a single, expertly edited source for all the methods they need.
Book Synopsis The logic of chemical synthesis by : E.J. Corey
Download or read book The logic of chemical synthesis written by E.J. Corey and published by Рипол Классик. This book was released on 1991 with total page 447 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Innovations in Chemical Biology by : Bilge Sener
Download or read book Innovations in Chemical Biology written by Bilge Sener and published by Springer Science & Business Media. This book was released on 2008-11-23 with total page 428 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book includes 49 chapters presented as plenary , invited lectures and posters at the conference. Six plenary lectures have published in an issue of Pure and Applied Chemistry, Vol. 79, No. 12, 2007; the titles of these presentations are given as an Annex at the end of the book. I thank all contrib utors for the preparation of their presentations. It is sad to report that Professor Hitoshi Ohtaki, one of the founders of the Eurasia conferences and contributors passed away on November 5, 2006. Professor Ohtaki enthusiastically promoted international cooperation and took it upon himself to p- licize Japanese science to the wider world. His contribution in this book will serve as a memorable contribution to that goal. He will be missed by all of us. This book is dedicated to his memory. Professor Dr . Bilge S ̧ ener Editor Memorial Tribute to Professor Dr. Hitoshi Ohtaki Curriculum Vitae of Hitoshi Ohtaki Date of Birth September 16, 1932 Place of Birth T ok yo, Japan Date of Decease November 5, 2006 (at the age of 74) Addr ess 3-9-406 Namiki-2-chome, Kanazawa-ku, Yokohama, Japan Institution Chair Professor of The Research Organization of Science and Engineering, Ritsumeikan University Guest Professor of Yokohama City University Education Bachelor of Science, Nagoya University, 1955 Master of Science, Nagoya University, 1957 Doctor of Science, Nagoya University, 1961 ix x Memorial Tribute to Professor Dr.
Book Synopsis Elements of Synthesis Planning by : R. W. Hoffmann
Download or read book Elements of Synthesis Planning written by R. W. Hoffmann and published by Springer Science & Business Media. This book was released on 2009-01-07 with total page 227 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthesis is at the core of organic chemistry. In order for compounds to be studied—be it as drugs, materials, or because of their physical properties— they have to be prepared, often in multistep synthetic sequences. Thus, the target compound is at the outset of synthesis planning. Synthesis involves creating the target compound from smaller, readily available building blocks. Immediately, questions arise: From which bui- ing blocks? In which sequence? By which reactions? Nature creates many highly complex “natural products” via reaction cascades, in which an asso- ment of starting compounds present within the cell is transformed by speci c (for each target structure) combinations of modular enzymes in speci c - quences into the target compounds [1, 2]. To mimic this ef ciency is the dream of an ideal synthesis [2]. However, we are at present so far from - alising such a “one-pot” operation that actual synthesis has to be achieved via a sequence of individual discrete steps. Thus, we are left with the task of planning each synthesis individually in an optimal fashion. Synthesis planning must be conducted with regard for certain speci - tions, some of which are due to the structure of the target molecule, and some of which relate to external parameters such as costs, environmental compatibility, or novelty. We will not consider these external aspects in this context. Planning of a synthesis is based on a pool of information regarding chemical reactions that can be executed reliably and in high chemical yield.
Book Synopsis Herbalism, Phytochemistry and Ethnopharmacology by : Amritpal Singh
Download or read book Herbalism, Phytochemistry and Ethnopharmacology written by Amritpal Singh and published by CRC Press. This book was released on 2011-04-11 with total page 440 pages. Available in PDF, EPUB and Kindle. Book excerpt: Bridging the gap between the ancient art of herbalism and the emerging sciences of ethnopharmocology and phytopharmacotherapy, this book highlights the major breakthroughs in the history of the field and focuses on future directions in the discovery and application of herb-derived medicines. Implementing the concept of reverse pharmacology, it inte
Book Synopsis Medicinal and Aromatic Plants by : Tariq Aftab
Download or read book Medicinal and Aromatic Plants written by Tariq Aftab and published by Springer Nature. This book was released on 2021-03-27 with total page 781 pages. Available in PDF, EPUB and Kindle. Book excerpt: Before the concept of history began, humans undoubtedly acquired life benefits by discovering medicinal and aromatic plants (MAPs) that were food and medicine. Today, a variety of available herbs and spices are used and enjoyed throughout the world and continue to promote good health. The international market is also quite welcoming for MAPs and essential oils. The increasing environment and nature conscious buyers encourage producers to produce high quality essential oils. These consumer choices lead to growing preference for organic and herbal based products in the world market. As the benefits of medicinal and aromatic plants are recognized, these plants will have a special role for humans in the future. Until last century, the production of botanicals relies to a large degree on wild-collection. However, the increasing commercial collection, largely unmonitored trade, and habitat loss lead to an incomparably growing pressure on plant populations in the wild. Therefore, medicinal and aromatic plants are of high priority for conservation. Given the above, we bring forth a comprehensive volume, “Medicinal and Aromatic Plants: Healthcare and Industrial Applications”, highlighting the various healthcare, industrial and pharmaceutical applications that are being used on these immensely important MAPs and its future prospects. This collection of chapters from the different areas dealing with MAPs caters to the need of all those who are working or have interest in the above topic.
Book Synopsis Himalayan Medicinal Plants by : Nikhil Malhotra
Download or read book Himalayan Medicinal Plants written by Nikhil Malhotra and published by Academic Press. This book was released on 2021-01-20 with total page 436 pages. Available in PDF, EPUB and Kindle. Book excerpt: The Himalayan Region is a mega hot spot for biological diversity. It supports over 1,748 plants species of known medicinal value. This title focuses on origin and distribution of Himalayan herbs, their medicinal potential, industrial significance, and research advancements pertaining to molecular breeding and omics-based approaches. - Discusses evolved secondary biochemical pathways often in response to specific environmental stimuli - Reviews conservation efforts - Presents an in-depth analysis of 12 key species
Book Synopsis Asymmetric Dearomatization Reactions by : Shu-Li You
Download or read book Asymmetric Dearomatization Reactions written by Shu-Li You and published by John Wiley & Sons. This book was released on 2016-09-13 with total page 422 pages. Available in PDF, EPUB and Kindle. Book excerpt: The first comprehensive account of the rapidly growing field of asymmetric dearomatization reactions with a focus on catalytic methods. It introduces the concept of dearomatization and describes recent progress in asymmetric reaction procedures with different catalyst systems, such as organocatalysts, transition metal catalysts, and enzymes. Chapters on dearomatizations of electron-deficient aromatic rings, dearomatization reactions via transition metal-catalyzed cross-couplings as well as dearomatization strategies in the synthesis of complex natural products are also included. Written by pioneers in the field, this is a highly valuable source of information not only for professional synthetic chemists in academia and industry but also for all those are interested in asymmetric methodologies and organic synthesis in general.
Book Synopsis Modern Methods in Stereoselective Aldol Reactions by : Rainer Mahrwald
Download or read book Modern Methods in Stereoselective Aldol Reactions written by Rainer Mahrwald and published by John Wiley & Sons. This book was released on 2013-02-22 with total page 604 pages. Available in PDF, EPUB and Kindle. Book excerpt: The selective formation of bondings between molecules is one of the major challenges in organic chemistry, and the so-called aldol reaction is one of the most important for this purpose. These reactions are a highly useful tool for developing such novel substances as natural products and pharmaceuticals. Likes its highly successful and much appreciated predecessor, "Modern Aldol Reactions", this ready reference provides a systematic overview of methodologies for installing a required configuration during an aldol addition step, but shifts the focus so as to cover the latest developments. As such, it presents a set of brand new tools, including vinylogous Mukaiyama-aldol reactions and substrate-controlled aldol reactions, as well as asymmetric induction in aldol additions. Furthermore, new developments in existing stereoselective aldol additions are described, such as the deployment of supersilyl groups or organocatalyzed aldol additions. All of these methodologies are presented in the context of their deployment in the total synthesis of natural products.
Book Synopsis Ranunculales Medicinal Plants by : Da-Cheng Hao
Download or read book Ranunculales Medicinal Plants written by Da-Cheng Hao and published by Academic Press. This book was released on 2018-04-23 with total page 406 pages. Available in PDF, EPUB and Kindle. Book excerpt: Ranunculales Medicinal Plants: Biodiversity, Chemodiversity and Pharmacotherapy comprehensively covers this order of flowering plants, detailing the phytochemistry, chemotaxonomy, molecular biology, and phylogeny of selected medicinal plants families and genera and their relevance to drug efficacy. The book carries out an exhaustive survey of the literature in order to characterize global trends in the application of flexible technologies. The interrelationship between Chinese species, and between Chinese and non-Chinese species, is inferred through molecular phylogeny and based on nuclear and chloroplast DNA sequencing. The book discusses the conflict between chemotaxonomy and molecular phylogeny in the context of drug discovery and development. Users will find invaluable and holistic coverage on the study of Ranunculales that will make this the go-to pharmaceutical resource. - Describes current perceptions of biodiversity and chemodiversity of Ranunculales - Explains how the conceptual framework of plant pharmacophylogeny benefits the sustainable exploitation of Ranunculales - Details how Ranunculales medicinal plants work from the chemical level upward - Covers how the polypharmacology of Ranunculales compounds might inspire new chemical entity design and development for improved treatment outcomes
Book Synopsis Branched-chain Amino Acids by : Robert Allison Harris
Download or read book Branched-chain Amino Acids written by Robert Allison Harris and published by Academic Press. This book was released on 2000 with total page 587 pages. Available in PDF, EPUB and Kindle. Book excerpt: Volume 324 of Methods in Enzymology supplements Volume 166. It includes genetic information (cloning, gene expression) and information on human genetic diseases not available when Volume 166 was published.
Book Synopsis Efficiency in Natural Product Total Synthesis by : Pei-Qiang Huang
Download or read book Efficiency in Natural Product Total Synthesis written by Pei-Qiang Huang and published by John Wiley & Sons. This book was released on 2018-07-24 with total page 512 pages. Available in PDF, EPUB and Kindle. Book excerpt: Uniting the key organic topics of total synthesis and efficient synthetic methodologies, this book clearly overviews synthetic strategies and tactics applied in total synthesis, demonstrating how the total synthesis of natural products enables scientific and drug discovery. • Focuses on efficiency, a fundamental and important issue in natural products synthesis that makes natural product synthesis a powerful tool in biological and pharmaceutical science • Describes new methods like organocatalysis, multicomponent and cascade reactions, and biomimetic synthesis • Appeals to graduate students with two sections at the end of each chapter illustrating key reactions, strategies, tactics, and concepts; and good but unfinished total synthesis (synthesis of core structure) before the last section • Compiles examples of solid phase synthesis and continuing flow chemistry-based total synthesis which are very relevant and attractive to industry R&D professionals
Download or read book Medicinal Plants written by Da-Cheng Hao and published by Woodhead Publishing. This book was released on 2015-06-29 with total page 694 pages. Available in PDF, EPUB and Kindle. Book excerpt: Medicinal Plants: Chemistry, Biology and Omics reviews the phytochemistry, chemotaxonomy, molecular biology, and phylogeny of selected medicinal plant tribes and genera, and their relevance to drug efficacy. Medicinal plants provide a myriad of pharmaceutically active components, which have been commonly used in traditional Chinese medicine and worldwide for thousands of years. Increasing interest in plant-based medicinal resources has led to additional discoveries of many novel compounds, in various angiosperm and gymnosperm species, and investigations on their chemotaxonomy, molecular phylogeny and pharmacology. Chapters in this book explore the interrelationship within traditional Chinese medicinal plant groups and between Chinese species and species outside of China. Chapters also discuss the incongruence between chemotaxonomy and molecular phylogeny, concluding with chapters on systems biology and "-omics technologies (genomics, transcriptomics, proteomics, and metabolomics), and how they will play an increasingly important role in future pharmaceutical research. - Reviews best practice and essential developments in medicinal plant chemistry and biology - Discusses the principles and applications of various techniques used to discover medicinal compounds - Explores the analysis and classification of novel plant-based medicinal compounds - Includes case studies on pharmaphylogeny - Compares and integrates traditional knowledge and current perception of worldwide medicinal plants
Book Synopsis Nutraceuticals in Brain Health and Beyond by : Dilip Ghosh
Download or read book Nutraceuticals in Brain Health and Beyond written by Dilip Ghosh and published by Academic Press. This book was released on 2020-11-12 with total page 478 pages. Available in PDF, EPUB and Kindle. Book excerpt: Nutraceuticals in Brain Health and Beyond focuses on a variety of health disorders where intervention with nutritional supplements prove valuable, such as Alzheimer's, Parkinson's, autism, and attention-deficit disorder in children. In addition, Nutraceuticals in Brain Health and Beyond addresses "herb-nutra psychiatry" which is a field of research focused on developing a comprehensive, cohesive, and scientifically rigorous evidence base to shift conceptual thinking around the role of diet and nutrition in mental health.Intended for nutrition researchers, nutritionists, dieticians, regulatory bodies, health professionals, and students studying related fields, Nutraceuticals in Brain Health and Beyond will be a useful reference in understanding the links between nutrition and brain health. - Addresses nutritional psychiatry and cognitive health at all stages of the lifespan - Contains extensive coverage of vitamins, minerals, botanicals, and other nutrients - Offers novel insight into cognitive dysfunctions including depression and other neurodegenerative disorders - Explores the role of genomics and epigenetics, including discussion of the gut–brain axis
