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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