TY  - BOOK
AU  - Morrow,Gary W.
TI  - Biorganic synthesis: an introduction 
SN  - 9780199860531
AV  - QD262 .M744 2016
U1  - 572/.45 23
PY  - 2016///]
CY  - New York, NY
PB  - Oxford University Press
KW  - Organic compounds
KW  - Synthesis
KW  - Biosynthesis
KW  - Chemistry, Organic
KW  - fast
N1  - Includes bibliographical references and index; Note continued; Study Problems --; Why We Synthesize Organic Compounds --; Synthetic Challenges: Total Synthesis --; Synthetic Challenges: Semisynthesis --; Synthetic Challenges: Biomimetic Synthesis --; Synthetic Challenges: Structural Revision or Confirmation --; Synthetic Challenges: Formal Synthesis --; Synthetic Challenges: Stereoselective Synthesis of Optically Pure Compounds --; Resolution of Enantiomers to Obtain Optically Pure Compounds --; Use of Chiral Pool Compounds for Synthesis of Optically Pure Natural Products --; Use of Chiral Reagents for Synthesis of Optically Pure Compounds --; Use of Chiral Substrate Control for Stereoselective Synthesis --; Use of Chiral Auxiliaries for Synthesis of Optically Pure Compounds --; Use of Chiral Catalysis for Synthesis of Optically Pure Compounds --; Use of Enzymes for Synthesis of Optically Pure Compounds: Biocatalysis --; Some Final Thoughts --; Study Problems; Machine generated contents note; The Unique Role of Carbon --; Distinguishing Primary Versus Secondary Metabolism --; Secondary Metabolites and Natural Products --; Natural Products in Organic Chemistry and Medicine --; The Organic Chemistry of Biosynthesis --; Goals and Structure of This Book --; Review of Functional Groups, Stereochemistry, and Conformational Analysis --; Prochiral Relationships: One Step from Chirality --; Prochiral it-Systems: "Two-Faced" Reaction Centers --; Diastereotopic Atoms and Groups: One Step from a Diasteroeomer --; Monosubstituted Cyclohexanes: Favoring Equatorial Positions --; Disubstituted Cyclohexanes: Equivalent and Nonequivalent Combinations --; Bicyclic Systems: Joining of Rings --; Heterocyclic Ring Systems: One Atom Makes All the Difference --; Bond Making and Breaking: Have Pair, Will Share; Need Two from You --; Bronsted Acid-Base Reactions: Proton Donors Gladly Accepted --; Acidity Trends: Why that Proton Is or Isn't Acidic --; Carbocations: Three Bonds to Carbon Can Be a Plus --; Radicals: Odd and Reactive --; Elimination Reactions: Introducing the Carbon-Carbon n-Bond --; Carbocations: Rearrangements and Fates --; Electrophilic Additions: n-Bonds as Nucleophilic Agents --; Nucleophilic Substitutions and Alkylations: Make or Break for C-X Bonds --; Nucleophilic Carbonyl Addition Reactions: C=O n-Bond under Attack --; Imine Formation: Making the Essential C=N Linkage --; Nucleophilic 1,4-(Conjugate) Addition Reactions: Remote Attack on Conjugated Carbonyls --; Nucleophilic Acyl Substitution Reactions: Turning One Acyl Compound into Another --; Looking Ahead --; Study Problems --; Enzymes: The Catalysts of Biological Organic Chemistry --; Cofactors: Enzyme Assistants in Bioorganic Reactions --; NADH/NADPH: Nature's Version of Sodium Borohydride for Carbonyl Reduction --; NAD+/NADP+: Nature's Version of PCC for Alcohol Oxidation --; FAD: Another Hydride Acceptor for Dehydrogenations --; Monooxygenases: Special Delivery of One 0 atom from 02 --; Dioxygenases: Delivering Both 0 Atoms from 02 --; Other Oxidations: Hydroquinone and Catechol Oxidations --; Amine Oxidations: From Imines to Carbonyl Compounds and Beyond --; PLP: Transamination and Decarboxylation of Amino Acids --; Other Important Decarboxylations: 13-Keto Acids, o- and p-Hydroxybenzoic Acids --; Thiamine Diphosphate (TPP) and Lipoic Acid: Decarboxylation and Acyl Transfer --; Biotin: The CO2 Carrier, Transport, and Transfer Agent --; SAM: A C1 Fragment for Methyl Groups --; DMAPP: An Allylic C, Fragment for Structure Building --; Other Essential Structural Fragments: Putting it All Together --; Looking Ahead --; Study Problems --; What Makes a Carbohydrate? --; Cyclic Hemiacetals and Anomers --; C-2 Epimers and Enediols[--]Simple Conversion of One Carbohydrate into Another --; Other Important Monosaccharides: Deoxy and Amino Sugars --; The Significance of the Anomeric Carbon: Glycoside Formation --; UDP-Sugars and Glycoside Formation: SN2 Chemistry at Work --; Organic Reactions in Carbohydrate Chemistry: Overview of Glucose Metabolism --; Glycolysis: A 10-Step Program --; What Happens to the Pyruvic Acid from Glycolysis --; The Citric Acid Cycle: Another 10-Step Program --; The Pentose Phosphate Pathway: Seven Alternative Steps to Some Familiar Intermediates --; The Big Picture --; Amino Acids: More Important Primary Metabolite Building Blocks for Biosynthesis --; Biosynthesis of Serine: A Good Place to Start --; Peptides and Proteins: A Very Brief Review --; Putting Proteins and Carbohydrates Together: Glycoproteins Versus Protein Glycosylation --; Looking Ahead --; Study Problems --; Classification of Terpenes: How Many Isoprene Units? --; The Mevalonic Acid Route to DMAPP and IPP --; The Deoxyxylulose Phosphate Route to IPP and DMAPP --; Hemiterpenes: Just One Isoprene Unit --; Monoterpenes (C10) and Isoprene Linkage: Heads, IPP Wins; Tails, DMAPP Loses --; Geranyl PP to Neryl PP via Linalyl PP: The Importance of Alkene Stereochemistry --; Some Acyclic Monoterpenes and Their Uses --; Mono- and Bicyclic Monoterpenes via Cationic Cyclizations and Wagner-Meerwein Shifts --; What's that Smell? Limonene Derivatives as Flavor and Fragrance Compounds --; Irregular Monoterpenes: If Not Head-to-Tail, then How? --; Iridoids: From Catnip to Alkaloids --; Sesquiterpenes (C15): Linking of Different Starter Units --; Some FPP Cyclizations in Sesquiterpene Biosynthesis --; Trichodiene and the Trichothecenes: How to Trace a Rearrangement Pathway --; Diterpenes (C20): Taking it to the Next Level of Molecular Complexity and Diversity --; Cyclic Diterpenes: From Baseball and Plant Hormones to Anticancer Drugs --; Sesterterpenes (C25): Less Common, More Complex --; Triterpenes and Steroids: Another Case of Irregular Linkage of Terpene Units --; Oxidosqualene and Steroid Biosynthesis: Cyclization to Lanosterol and Beyond --; Conversion of Lanosterol (C30) to Cholesterol (C27): Where Did the Carbons Go? --; Conversions of Cholesterol: Production of the Sex Hormones --; Dehydrocholesterol, Sunshine, and Vitamin D3 Biosynthesis --; Tetraterpenes and Carotenoids: Tail-to-Tail Linkage of C20 Units --; Looking Ahead --; Study Problems --; Fatty Acids: Multiples of Two Carbons, Saturated or Unsaturated --; Saturated Fatty Acid Biosynthesis: It All Starts with Acetyl-CoA --; Branched Fatty Acids: Different Routes and Different Results --; Mono- and Polyunsaturated Fatty Acids: Putting in the "Essential" Double Bonds --; Aerobic Versus Anaerobic Routes to Desaturation --; Further Desaturation of Fatty Acids: Triple Bonds and Rings --; Prostaglandins, Thromboxanes, and Leukotrienes: The Power of Oxygenated FAs --; Polyketide Biosynthesis: More Starter Units and Extender Units, but with a Twist --; Aromatic Polyketide Natural Products: Phenols and Related Structures --; Isotopic Labeling Studies: Biosynthetic Insights via 13C NMR --; Further Modification of Polyketides: Alkylations, Oxidations, Reductions, and Decarboxylations --; Other Oxidative Modifications of Aromatic Rings: Expansion or Cleavage Processes --; Oxidative Coupling of Phenols: Formation of Aryl-Aryl Bonds --; The Use of Other Starter Groups: From Cancer Drugs and Antibiotics to Poison Ivy --; More on Polyketide Synthase (PKS) Systems: Increasing Product Diversity --; Modular Type I PKS Complexes and Macrolide Antibiotics: Erythromycin Biosynthesis --; Genetic Manipulation of Modular PKS Systems: Rational Drug Modification --; Some Final PKS Products of Medicinal Importance --; Looking Ahead --; Study Problems --; What Is Shikimic Acid? --; Shikimic, Chorismic, and Prephenic Acids at the Heart of the Pathway --; The Claisen Rearrangement: Allyl Vinyl Ethers in a Chair --; Conversion of Chorismic Acid to Prephenic Acid --; Conversion of Prephenic Acid to Phenylalanine or Tyrosine --; More Uses for Chorismic Acid --; Shikimic Acid Pathway Products from Phenylalanine and Tyrosine: An Overview --; Phenylpropanoids: A Large Family of Phenyl C3 Compounds --; Phenylpropanoids: Reduction of Acids to Phenyl C3 Aldehydes and Alcohols --; Reduction of Phenyl C3 Alcohols to Phenylpropenes --; Lignans and Lignin: Oxidative Phenolic Coupling with a Twist --; Coniferyl Alcohol Oxidative Coupling: Allyl C-Radical + Allyl C-Radical --; Coniferyl Alcohol Oxidative Coupling: Ortho C-Radical + Allyl C-Radical --; Coniferyl Alcohol Oxidative Coupling: O-Radical + Allyl C-Radical --; Lignin: A Plant Polymer and Major Source of Carbon --; Podophyllotoxin Biosynthesis: Aryltetralin Lignans from the American Mayapple --; Cleavage of Cinnamic Acids to Phenyl Cl Compounds: Different Routes, Similar Outcomes --; Coumarins: Sweet-Smelling Benzopyrones --; Mixed Products: Combining the Shikimate, Polyketide, and Terpenoid Pathways --; Kavalactones: Natural Sedatives from the South Pacific --; Flavonoids: Structurally Diverse Plant Polyphenolics --; The Chalcone-to-Flavanone-to-Flavone Sequence: Formation of Apigenin --; The Flavanone-to-Dihydroflavonol-to-Anthocyanin Sequence: Formation of Pelargonidin --; The Flavanone-to-Isoflavanone-to-Isoflavone Sequence: Formation of Genistein --; Isoflavanoid Structural Modifications: Production of Antimicrobial Phytoalexins --; Rotenoids: Fish Poisons from Isoflavones --; Looking Ahead --; Study Problems --; Alkaloid Structure: The Importance of N-Heterocycles --; Alkaloids Not Derived from Amino Acids: Amination Reactions, Poisons, and Venoms --; Amino Acids and Mannich; Reactions: Important Keys to Alkaloid Biosynthesis --; Alkaloids from Ornithine: Tropanes via the Mannich Reaction in Action --; Pyrrolizidine Alkaloids: Poison Plants and Insect Defense --; Piperidine-Type Alkaloids Derived from Lysine --; Quinolizidine Alkaloids: Livestock Poisons from Cadaverine --; Alkaloids from Phenylalanine: From Neurotransmitters to Decongestants and Narcotics --; Alkaloids from Tyrosine: The Pictet-Spengler Reaction in Alkaloid Biosynthesis --; (S)-Reticuline: A Versatile Pictet-Spengler-Derived Benzyltetrahydroisoquinoline --; Oxidative Coupling in Alkaloid Biosynthesis: Biosynthesis of Corytuberine and Morphine --; The Morphine Rule --; Alkaloids from Tryptophan: Adventures in Indole Alkaloid Structural Complexity --; Pictet-Spengler-Type Reactions of Tryptamine: p-Carbolines and Indole Terpene Alkaloids --; Alkaloids from Nicotinic Acid: Toxic Addictive Derivatives of a Common Nutrient --; Alkaloids from Anthranilic Acid: From Tryptophan to Quinolines and Acridines --; Alkaloids from Histidine: From Simple Amides to Glaucoma Drugs --; Purine Alkaloids: Addictive Stimulants in our Coffee, Tea, and Chocolate --; Cyclic and Macrocyclic Peptides: From Sweeteners to Antibiotics and Beyond --; Penicillins, Cephalosporins, and Carbapenums: The Essential p-Lactam Antibiotics --; A Final Look Ahead
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