Fortschritte der Chemie organischer Naturstoffe 80 / Progress in the Chemistry of Organic Natural Products

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C. W. J. Chang
542 g
229x152x19 mm
80, Progress in the Chemistry of Organic Natural Products
Naturally Occurring Isocyano/Isothiocyanato and Related Compounds.- 1. Introduction.- 1.1. Occurrence and Distribution.- 1.2. Nomenclature and Structural Representation.- 1.3. Isolation and Identification.- 1.3.1. Physical and Chemical Properties.- 1.3.2. Spectral Characterization.- 2. Monoterpene Indole Alkaloids from Blue-Green Algae.- 2.1. C21-Compounds.- 2.1.1. Hapalindolcs.- 2.1. 1. 1. Tetracyclic Hapalindoles 1.- Tricyclic Hapalindoles 1.- 2.1.2. Fischerindoles.- 2.2. Oxindoles and Modified Oxygenated C'21-Indoles.- 2.2.1. Hapaloxindoles.- 2.2.2. Hapalonamides.- 2.2.3. Hapalindolinones.- 2.2.4. Welwitindolinoncs.- 2.3. C26-Indole Alkaloids.- 2.3.1. Ambiguine Isonitriles.- 2.4. Reactions of Hapalindoles.- 2.5. Syntheses of Hapalindolcs.- 3. Marine Diterpenes from Sponges.- 3.1. Acyclics.- 3.2. Kalihinanes.- 3.2.1. Kalihinols from Actin/he/hi Sponges.- 3.2.2. Tetrahydropyrans.- 3.2.3. Tetrahydrofurans.- 3.2.4. Dihydropyrans.- 3.3. Amphilectanes.- 3.3.1. Isocyanoditcrpencs from Crnihastela hooperi.- 3.3.2. Amphilectanes.- 3.3.3. Cycloamphilectanes.- 3.3.4. Isocycloamphilectanes.- 3.3.5. Veo-and "Prc"-amphilcctadicncs.- 3.4. Diterpene Syntheses.- 4. Marine Sesquiterpenes from Sponges.- 4.1. Skeletal Types.- 4.2. The Triads from Axinella cannabina.- 4.3. Sesquiterpenoid Compounds.- 4.3.1. Axanes.- 4.3.2. Aromadendranes.- 4.3.3. Eudesmanes.- 4.3.4. Cadinanes.- 4.3.5. Epimaalianes.- 4.3.6. Spiroaxanes.- 4.3.7. Bisbolanes.- 4.3.8. Guaiane-Types.- 4.3.9. Pupukeanane-Types.- 4.4. Sesquiterpene Syntheses.- 5. Uncommon Marine Analogs.- 5.1. Carbonimidic Dichloride Terpenes.- 5.2. Isothiocyanato and Thiocyanato Nonterpenoids.- 5.2.1. Ascidians.- 5.2.2. Sponges.- 5.3. Marine Cyanides.- 6. Other Terrestrial Compounds.- 6.1. Isocyanides from Lower Organisms.- 6.1.1. Xanthocillins.- 6.1.2. Cyclopentanes.- Dermadin-Types 12.- Trichoviridin-Types 12.- 6.2. Other Terrestrial Isocyanides.- 6.3. Other Terrestrial Analogs.- 6.4. Syntheses of Terrestrial Isocyanides.- 7. Biogenesis and Biosynthesis.- 7.1. Monoterpene Indole Alkaloids.- 7.2. Diterpenes.- 7.3. Sesquiterpenes.- 7.4. Other Terrestrial Isocyanides and Isothiocyanates.- 8. Discussion and Summary.- Addendum.- Acknowledgment.- References.- Sulfur-Containing Amides from Glycosmis Species (Rutaceae).- I. Introduction.- 2. Isolation and Structure Elucidation.- 2.1. Analytical HPLC and Preparative MPLC.- 2.2. Structure Elucidation and Stereochemistry.- 3. Methylthiopropenoic Acid Amides.- 4. Methylsulfinylpropenoic Acid Amides.- 5. Methylsulfonylpropenoic Acid Amides.- 5.1. p-Prenyloxyphenethylamides.- 5.2. O-Geranyltyramides.- 5.3. p-O-Geranyldopamides.- 5.4. 13-Hydroxy-O-geranyltyramides.- 6. Methylthiocarbonic Acid Amides.- 7. Synthesis of Biogenic Sulfur-Containing Amides.- 8. Biological Activity.- 9. Biosynthesis.- 10. Chemotaxonomy.- Appendix: Sulfur-Containing Bisamides from Aglaia Species (Meliaceae).- References.- Author Index.
Glycosmis is a clearly defined genus within the tribe Clauseneae of the Aurantioideae subfamily of the family Rutaceae comprising about 40 species (1). Its range of distribution is centered in south and southeast Asia (India, Sri Lanka, Myanmar, Thailand, Malaysia, Indonesia) and extends to south China and Taiwan as well as to New Guinea and north Australia. Exceptions are only cultivated species like the Chinese G. parvijiora (Sims) Little, formerly called G. citrifolia (Willd. ) Lindley, which became naturalized in tropical America and Africa (Angola) (1). The shrubs or small trees are unarmed and possess pinnate or simple leaves with translucent punctate glands emitting an aromatic odor when crushed. The axillary inflorescences are usually dispersed closed panicles with small white flowers. The fruits are mostly pink, reddish or white berries of about I cm in diameter with only one or two seeds. The genus name Glycosmis originates from the sweet smell of the flowers and the sweet taste of the fleshy pericarp of the fruits. A good field and herbarium character of the genus is that the buds of new leaves are usually covered with short rusty-red hairs. In spite of the good delimitation of Glycosmis from the other closely related Clauseneae genera Clausena, Micromelum, Murraya, and Merrillia and the already existing subrevisionary treatment by Stone (1), there are still many unresolved taxonomic problems at the species level.