New Results on the Chemistry of Lichen Substances
Lichen chemistry continues to be a flourishing branch of natural product chemistry. Since the last major review by Elix et al. in volume 35 of this series (274 ) many new and interesting lichen substances have been isolated and synthesized. This suggests
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Contents Abbreviations
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I. Introduction
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2. Methods for Identification and Structure Elucida tion of Lichen Substances . . .
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2.1. 2.2. 2.3. 2.4. 2.5. 2.6. 2.7. 2.8. 2.9. 2.10. 2.11.
Spot Tests Thin Layer Chrom atog raphy (TLC) High Performan ce Liquid Chromatograph y (HPLC) Droplet Count er-Current Chromatography NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Mass Spectrometry X-ray Analysis Cathodoluminescence and X-ray Microanalysis Laser Microprobe Mass Spectromet ry (LAMMA) .......... Fluorescence Microscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Computer Progr am for Identification of Lichen Substances (WINTABOLITES)
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3. General Methods for Derivati zation and Regeneration of Lichen Substances . .
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3.1. Carbox yl Group s 3.1.1. Methylation 3.1.2. Benzylation and Debenzylation 3.1.3. Carb oxylation and Decarb oxylation 3.2. Alcoholic and Phenolic Groups 3.2.1. Acetylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 3.2.2. Methylation and Demethylation . . . . . . . . . . . . . . . . . . . . . . . . . 3.2.3. Isoprop ylation and Deisoprop ylation 3.2.4. Benzylation and Debenzylation 3.2.5. Oxidation of Alcohols
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S. Huneck, Fortschritte der Chemie organischer Nuturstoffe © Springer-Verlag Wien 2001
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S. Hun eck 3.3. Substitution at Aro matic Rings 3.3.1. Halogenation and Dehalogenation 3.3.2. Hydroxylat ion . . . . . . . . . . . . . . . . . . 3.4. Synthesis of Aldehydes 3.4.1. Reduction of Aldehydes . . . . . . . . . . . 3.4.2. Oxidation of Aldehydes . . . . . . . . . . . 3.5. Cleavage and Fo rmat ion of the Depside Ester
.................... .................... Bond
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4. Structure Elucidati on and Synthesis of Lichen Substances . . . . . . . . . . . . . ..
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4. 1. 4.2. 4.3. 4.4.
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Nitrogen Conta ining Compounds . . . . . . . . . . . . . . . . . Phosphoru s Co ntaining Compounds . . . . . . . . . . . . . . . Polyols, Mono- and Polysaccharides and Ca rbohydra tes Alipha tic and Cycloaliphatic Compounds . . . . . . . . . . . 4.4.1. Hydrocarb ons . . . . . . . . . . . . . . . . . . . . . . . . . . 4.4.2. Aliphat ic Alcohols . . . . . . . . . . . . . . . . . . . . . . . 4.4.3. Aliphatic Acids and Esters . . . . . . . . . . . . . . . . . 4.4.4. Aliphat ic Tr icarb oxylic Acids . . . . . . . . . . . . . . . 4.4.5. y-Lactonic Acids . . . . . . . . . . . . . . . . . . . . . . . . 4.4.6. Macrocyclic Lactones and Bis-Lactones . . . . . . . . 4.4.6.1. Aspicilin . . . . . . . . . . . . . . . . . . . . . . . . 4.4.6.2. Lepranth in 4.4.7. Anh ydrides . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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4.5. Aromatic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.5.1. Aro matic Units . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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