Table of Contents

List of Contributors.- Synthetic Aspects of Iridoid Chemistry.- 1. Introduction.- 2. Classification of Iridoids.- 2.1. Iridoid Glycosides.- 2.2. Non-Glycosidic Iridoids.- 2.3. Nitrogen-Containing Compounds.- 3. Availability and Production of Iridoids.- 3.1. Plant Sources.- 3.2. Cell-Cultures.- 3.3. Isolation and Purification Methods.- 4. Semi-Synthetic Conversions Between Iridoids.- 4.1. Hydrolysis and Lactonization.- 4.2. Decarboxylation of Iridoid Glucosides.- 4.3. Reduction and Oxidation of Iridoid Glucosides.- 4.4. Miscellaneous Transformations Used in Structure Elucidation.- 4.5. Non-Glucosidic Iridoids.- 4.6. Ring-Cleavage Sequences and Secoiridoid Chemistry.- 5. Monoterpene Alkaloids Structurally Related to lridoids.- 5.1. PMTAs - Natural Compounds or Artifacts?.- 5.2. Semi-Synthesis of Pyridine Monoterpene Alkaloids.- 5.3. Bacterial Metabolism of Iridoid Glucosides.- 5.4. Total Synthesis of Pyridine Monoterpene Alkaloids.- 5.5. Diversity of Bicyclic Cyclopentanoid Piperidines.- 5.6. Synthesis of Bicyclic Cyclopentanoid Piperidines.- 5.7. Semi-Synthesis of Glucosidic Secoiridoid Alkaloids.- 6. Syntheses from Iridoids.- 6.1. Formation of Colored Compounds.- 6.2. Reactions of Secoiridoids.- 6.3. Preparation of Marine Diterpenoids.- 6.4. Building Blocks for Other Types of Cyclopentanoids.- 6.5. Modifications of the Sugar Moiety in Iridoid Glucosides.- References.- The Defensive Chemistry of Ants.- 1. Introduction.- 2. Alkaloids.- 2.1. Structures, Occurrence, and Function.- 2.1.1. Piperidines and Pyridines.- 2.1.2. Pyrrolidines and Pyrrolines.- 2.1.3. Pyrrolizidines.- 2.1.4. Indolizidines.- 2.1.5. Tetraponerines.- 2.1.6. Other Alkaloids.- 2.2. Synthesis.- 2.2.1. Piperidines.- 2.2.2. Pyrrolidines.- A. Synthesis of Racemic Pyrrolidines 13.- B. Syntheses of Nonracemic Pyrrolidines 13.- 2.2.3. Pyrrolines.- 2.2.4. Pyrrolizidines.- 2.2.4.1. 3,5-Dialkylpyrrolizidines 15.- A. Xenovenine.- B. (5E,8E)-3-Butyl-5-hexylpyrrolizidine.- 2.2.4.2. 3-Methyl-5-alkenylpyrrolizidines and 3,5-Dialkenylpyrrolizidines 16.- 2.2.5. Indolizidines.- 2.2.5.1. Monomorine I 16.- A. Syntheses of Racemic Monomorine I.- B. Syntheses of Nonracemic Monomorine I.- 2.2.5.2. 3,5-Dialkylindolizidines 19.- A. 3-Butyl-5(4-penten-l-yl)indolizidine.- B. 3-Ethyl- and 3-Hexyl-5-methylindolizidines.- C. Myrmicarin 237A and 237B.- D. Myrmicarin 217.- 2.2.6. Tetraponerines.- A. Syntheses of Racemic Tetraponerines 20.- B. Syntheses of Nonracemic Tetraponerines 20.- 3. Nonalkaloidal Compounds.- 4. Biosynthesis.- References.