Author: Eduardo Valentin Mercado-Marin
Publisher:
ISBN:
Category :
Languages : en
Pages : 356
Book Description
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.
A Unified Approach Toward the Total Syntheses of Prenylated Indole Alkaloid Natural Products
Author: Eduardo Valentin Mercado-Marin
Publisher:
ISBN:
Category :
Languages : en
Pages : 356
Book Description
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.
Publisher:
ISBN:
Category :
Languages : en
Pages : 356
Book Description
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.
A Unified Approach Toward the Total Synthesis of Lycopodium Alkaloids of the Miscellaneous Class
Author: Sarah Elizabeth House
Publisher:
ISBN:
Category :
Languages : en
Pages : 370
Book Description
A unified approach to the total synthesis of Lycopodium alkaloids belonging to the miscellaneous class has been developed, wherein a single tetracyclic amine is employed as a common intermediate in synthetic studies toward several alkaloids. An overview of Lycopodium alkaloids is presented, including their structural classification, isolation and biological activity. The biosynthesis of alkaloids in the miscellaneous group is discussed in depth. A summary of previous synthetic work focusing on miscellaneous Lycopodium alkaloids is presented, including total syntheses of luciduline, lyconadins A and B and nankakurines A and B.A model study of spirolucidine is discussed. A biomimetic route to access spirolucidine and nankakurine B has been investigated. In this study, a tetracyclic amine that is a key intermedite in the total synthesis of lyconadin A previously developed in our laboratory is elaborated into a tertiary alcohol that mimics the proposed biosynthetic precursor of nankakurine B.A biomimetic ring-contractive [alpha]-hydroxyimine rearrangement to generate nankakurine B has been extensively investigated and found to be disfavored. The conversion of a tricyclic ketone (first synthesized en route to lyconadin A) to the tetracyclic core of serratezomine D has been investigated. The core of this molecule was inaccessible via methods employed in the studies toward lyconadin A. The total synthesis of 1'-epi-dihydrolycolucine from the key common tetracyclic amine intermediate has been achieved. Studies toward the synthesis of serratezomine E served as a platform to develop this method and to determine the stereochemical outcome of this reaction.
Publisher:
ISBN:
Category :
Languages : en
Pages : 370
Book Description
A unified approach to the total synthesis of Lycopodium alkaloids belonging to the miscellaneous class has been developed, wherein a single tetracyclic amine is employed as a common intermediate in synthetic studies toward several alkaloids. An overview of Lycopodium alkaloids is presented, including their structural classification, isolation and biological activity. The biosynthesis of alkaloids in the miscellaneous group is discussed in depth. A summary of previous synthetic work focusing on miscellaneous Lycopodium alkaloids is presented, including total syntheses of luciduline, lyconadins A and B and nankakurines A and B.A model study of spirolucidine is discussed. A biomimetic route to access spirolucidine and nankakurine B has been investigated. In this study, a tetracyclic amine that is a key intermedite in the total synthesis of lyconadin A previously developed in our laboratory is elaborated into a tertiary alcohol that mimics the proposed biosynthetic precursor of nankakurine B.A biomimetic ring-contractive [alpha]-hydroxyimine rearrangement to generate nankakurine B has been extensively investigated and found to be disfavored. The conversion of a tricyclic ketone (first synthesized en route to lyconadin A) to the tetracyclic core of serratezomine D has been investigated. The core of this molecule was inaccessible via methods employed in the studies toward lyconadin A. The total synthesis of 1'-epi-dihydrolycolucine from the key common tetracyclic amine intermediate has been achieved. Studies toward the synthesis of serratezomine E served as a platform to develop this method and to determine the stereochemical outcome of this reaction.
Synthesis of Indole Alkaloids
Author: Reuben Murray White
Publisher:
ISBN:
Category : Drug development
Languages : en
Pages : 258
Book Description
Publisher:
ISBN:
Category : Drug development
Languages : en
Pages : 258
Book Description
Medicinal Natural Products
Author: Paul M. Dewick
Publisher: John Wiley & Sons
ISBN: 9780471496410
Category : Medical
Languages : en
Pages : 524
Book Description
This guide covers classes of natural products in medicine, whether derived from plants, micro-organisms or animals. Structured according to biosynthetic pathway, it is written from a chemistry-based approach.
Publisher: John Wiley & Sons
ISBN: 9780471496410
Category : Medical
Languages : en
Pages : 524
Book Description
This guide covers classes of natural products in medicine, whether derived from plants, micro-organisms or animals. Structured according to biosynthetic pathway, it is written from a chemistry-based approach.
Natural Product Biosynthesis
Author: Christopher T. Walsh
Publisher: Royal Society of Chemistry
ISBN: 1788010760
Category : Science
Languages : en
Pages : 787
Book Description
This textbook describes the types of natural products, the biosynthetic pathways that enable the production of these molecules, and an update on the discovery of novel products in the post-genomic era.
Publisher: Royal Society of Chemistry
ISBN: 1788010760
Category : Science
Languages : en
Pages : 787
Book Description
This textbook describes the types of natural products, the biosynthetic pathways that enable the production of these molecules, and an update on the discovery of novel products in the post-genomic era.
Plant-derived Natural Products
Author: Anne E. Osbourn
Publisher: Springer Science & Business Media
ISBN: 0387854983
Category : Science
Languages : en
Pages : 588
Book Description
Plants produce a huge array of natural products (secondary metabolites). These compounds have important ecological functions, providing protection against attack by herbivores and microbes and serving as attractants for pollinators and seed-dispersing agents. They may also contribute to competition and invasiveness by suppressing the growth of neighboring plant species (a phenomenon known as allelopathy). Humans exploit natural products as sources of drugs, flavoring agents, fragrances and for a wide range of other applications. Rapid progress has been made in recent years in understanding natural product synthesis, regulation and function and the evolution of metabolic diversity. It is timely to bring this information together with contemporary advances in chemistry, plant biology, ecology, agronomy and human health to provide a comprehensive guide to plant-derived natural products. Plant-derived natural products: synthesis, function and application provides an informative and accessible overview of the different facets of the field, ranging from an introduction to the different classes of natural products through developments in natural product chemistry and biology to ecological interactions and the significance of plant-derived natural products for humans. In the final section of the book a series of chapters on new trends covers metabolic engineering, genome-wide approaches, the metabolic consequences of genetic modification, developments in traditional medicines and nutraceuticals, natural products as leads for drug discovery and novel non-food crops.
Publisher: Springer Science & Business Media
ISBN: 0387854983
Category : Science
Languages : en
Pages : 588
Book Description
Plants produce a huge array of natural products (secondary metabolites). These compounds have important ecological functions, providing protection against attack by herbivores and microbes and serving as attractants for pollinators and seed-dispersing agents. They may also contribute to competition and invasiveness by suppressing the growth of neighboring plant species (a phenomenon known as allelopathy). Humans exploit natural products as sources of drugs, flavoring agents, fragrances and for a wide range of other applications. Rapid progress has been made in recent years in understanding natural product synthesis, regulation and function and the evolution of metabolic diversity. It is timely to bring this information together with contemporary advances in chemistry, plant biology, ecology, agronomy and human health to provide a comprehensive guide to plant-derived natural products. Plant-derived natural products: synthesis, function and application provides an informative and accessible overview of the different facets of the field, ranging from an introduction to the different classes of natural products through developments in natural product chemistry and biology to ecological interactions and the significance of plant-derived natural products for humans. In the final section of the book a series of chapters on new trends covers metabolic engineering, genome-wide approaches, the metabolic consequences of genetic modification, developments in traditional medicines and nutraceuticals, natural products as leads for drug discovery and novel non-food crops.
Cascade Biocatalysis
Author: Sergio Riva
Publisher: John Wiley & Sons
ISBN: 3527682511
Category : Science
Languages : en
Pages : 587
Book Description
This ready reference presents environmentally friendly and stereoselective methods of modern biocatalysis. The experienced and renowned team of editors have gathered top international authors for this book. They cover such emerging topics as chemoenzymatic methods and multistep enzymatic reactions, while showing how these novel methods and concepts can be used for practical applications. Multidisciplinary topics, including directed evolution, dynamic kinetic resolution, and continuous-flow methodology are also discussed. From the contents: * Directed Evolution of Ligninolytic Oxidoreductases: from Functional Expression to Stabilization and Beyond * New Trends in the In Situ Enzymatic Recycling of NAD(P)(H) Cofactors * Monooxygenase-Catalyzed Redox Cascade Biotransformations * Biocatalytic Redox Cascades Involving w-Transaminases * Multi-Enzyme Systems and Cascade Reactions Involving Cytochrome P450 Monooxygenases * Chemo-Enzymatic Cascade Reactions for the Synthesis of Glycoconjugates * Synergies of Chemistry and Biochemistry for the Production of Beta-Amino Acids * Racemizable Acyl Donors for Enzymatic Dynamic Kinetic Resolution * Stereoselective Hydrolase-Catalyzed Processes in Continuous-Flow Mode * Perspectives on Multienzyme Process Technology * Nitrile Converting Enzymes Involved in Natural and Synthetic Cascade Reactions * Mining Genomes for Nitrilases * Key-Study on the Kinetic Aspects of the In-Situ NHase/AMase Cascade System of M. imperiale Resting Cells for Nitrile Bioconversion * Enzymatic Stereoselective Synthesis of Beta-Amino Acids * New Applications of Transketolase: Cascade Reactions for Assay Development * Aldolases as Catalyst for the Synthesis of Carbohydrates and Analogs * Enzymatic Generation of Sialoconjugate Diversity * Methyltransferases in Biocatalysis * Chemoenzymatic Multistep One-Pot Processes
Publisher: John Wiley & Sons
ISBN: 3527682511
Category : Science
Languages : en
Pages : 587
Book Description
This ready reference presents environmentally friendly and stereoselective methods of modern biocatalysis. The experienced and renowned team of editors have gathered top international authors for this book. They cover such emerging topics as chemoenzymatic methods and multistep enzymatic reactions, while showing how these novel methods and concepts can be used for practical applications. Multidisciplinary topics, including directed evolution, dynamic kinetic resolution, and continuous-flow methodology are also discussed. From the contents: * Directed Evolution of Ligninolytic Oxidoreductases: from Functional Expression to Stabilization and Beyond * New Trends in the In Situ Enzymatic Recycling of NAD(P)(H) Cofactors * Monooxygenase-Catalyzed Redox Cascade Biotransformations * Biocatalytic Redox Cascades Involving w-Transaminases * Multi-Enzyme Systems and Cascade Reactions Involving Cytochrome P450 Monooxygenases * Chemo-Enzymatic Cascade Reactions for the Synthesis of Glycoconjugates * Synergies of Chemistry and Biochemistry for the Production of Beta-Amino Acids * Racemizable Acyl Donors for Enzymatic Dynamic Kinetic Resolution * Stereoselective Hydrolase-Catalyzed Processes in Continuous-Flow Mode * Perspectives on Multienzyme Process Technology * Nitrile Converting Enzymes Involved in Natural and Synthetic Cascade Reactions * Mining Genomes for Nitrilases * Key-Study on the Kinetic Aspects of the In-Situ NHase/AMase Cascade System of M. imperiale Resting Cells for Nitrile Bioconversion * Enzymatic Stereoselective Synthesis of Beta-Amino Acids * New Applications of Transketolase: Cascade Reactions for Assay Development * Aldolases as Catalyst for the Synthesis of Carbohydrates and Analogs * Enzymatic Generation of Sialoconjugate Diversity * Methyltransferases in Biocatalysis * Chemoenzymatic Multistep One-Pot Processes
Total Synthesis of Natural Products
Author: Jie Jack Li
Publisher: Springer Science & Business Media
ISBN: 3642340652
Category : Science
Languages : en
Pages : 292
Book Description
'Total Synthesis of Natural Products' is written and edited by some of today's leaders in organic chemistry. Eleven chapters cover a range of natural products, from steroids to alkaloids. Each chapter contains an introduction to the natural product in question, descriptions of its biological and pharmacological properties and outlines of total synthesis procedures already carried out. Particular emphasis is placed on novel methodologies developed by the respective authors and their research groups. This text is ideal for graduate and advanced undergraduate students, as well as organic chemists in academia and industry.
Publisher: Springer Science & Business Media
ISBN: 3642340652
Category : Science
Languages : en
Pages : 292
Book Description
'Total Synthesis of Natural Products' is written and edited by some of today's leaders in organic chemistry. Eleven chapters cover a range of natural products, from steroids to alkaloids. Each chapter contains an introduction to the natural product in question, descriptions of its biological and pharmacological properties and outlines of total synthesis procedures already carried out. Particular emphasis is placed on novel methodologies developed by the respective authors and their research groups. This text is ideal for graduate and advanced undergraduate students, as well as organic chemists in academia and industry.
Biochemistry and Molecular Biology of Plants
Author: Bob B. Buchanan
Publisher: John Wiley & Sons
ISBN: 0470714220
Category : Science
Languages : en
Pages : 1280
Book Description
With over 1000 original drawings and 500 photographs, this work offers complete coverage of cell biology, plant physiology and molecular biology.
Publisher: John Wiley & Sons
ISBN: 0470714220
Category : Science
Languages : en
Pages : 1280
Book Description
With over 1000 original drawings and 500 photographs, this work offers complete coverage of cell biology, plant physiology and molecular biology.
Bioactive Heterocycles V
Author: Mahmud Tareq Hassan Khan
Publisher: Springer
ISBN: 3540734066
Category : Science
Languages : en
Pages : 342
Book Description
With contributions by numerous experts
Publisher: Springer
ISBN: 3540734066
Category : Science
Languages : en
Pages : 342
Book Description
With contributions by numerous experts