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  • 1
    Digitale Medien
    Digitale Medien
    Cameroonane, Prenopsane and Nopsane, Three New Tricyclic Sesquiterpene Skeletons (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1205-1212 
    Details
    ISSN: 1434-193X
    Schlagwort(e): New tricyclic sesquiterpene alcohols ; Natural products ; Essential oil ; Compositae ; Odoriferous substances ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The strong patchouli-like and woody smelling essential oil of the rhizomes of Echinops giganteus var. lelyi C. D. Adams (Compositae) contains only sesquiterpenes, which are mainly triquinanes. Besides the known tricyclic compounds, silphiperfol-5- (1, 3) and -6-ene (4), modhephen-2-ene (5), α- (6) and β-isocomene (7), silphiperfolan-7β-ol (12), presilphiperfolan-8-ol (13), silphiperfol-6-en-5-one (14) and 7-epi-silphiperfolan-6β-ol (20), the following compounds, three of which (15, 17, 18) have new skeletons, were found, for the first time, occurring naturally: presilphiperfol-7-ene (2), cameroonan-7-ol (15), an 11(7→8)-abeo-presilphiperfolan-7-ol, prenopsan-8-ol (17), a 1(8→7)-abeo-cameroonan-8-ol, and nopsan-4-ol (18), a 3(4→8)-abeo-prenopsan-4-ol, three diastereomers of silphiperfolan-6-ol (19, 21, 22), modheph-2-en-8-ol (23) and silphiperfola-4,7(14)-diene (24). All structures were elucidated by NMR spectroscopy. A biogenetic pathway from a presilphiperfolane cation C to the cameroonane K, prenopsane L and nopsane M cations is shown. Cameroonanol (15) and prenopsanol (17) are the main contributors to the fragrance of the total oil.
    Materialart: Digitale Medien
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  • 2
    Digitale Medien
    Digitale Medien
    Terpenes and Terpene Derivatives, XXV. Oreodaphnenol - A Sesquiterpene Alcohol with a New Carbon Skeleton (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 307-308 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Essential oil ; Phoebe oil ; Lauraceae ; Oreodaphne porosa ; Sesquiterpenes ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: From the essential oil of Oreodaphne porosa (commercial “Phoebe oil”) a sesquiterpene alcohol with a new carbon skeleton, oreodaphnenol (1), could be isolated. The structure and relative stereochemistry were deduced from detailed NMR studies and by degradation to the ketone 2.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.198919890154
    Bibliothek Standort Signatur Band/Heft/Jahr Verfügbarkeit
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  • 3
    Digitale Medien
    Digitale Medien
    Terpenes and Terpene Derivatives, XXVIII. New Monoterpene Derivatives from the Essential Oil of Artemisia salsoloides (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 279-281 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Artemisia salsoloides ; Essential oil ; 4-Oxogeranyl acetate ; Furomyrcenol ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: From the essential oil of Artemisia salsoloides the oxygenated monoterpenes 1, and 3-8 could be isolated. The easy formation of the hydroperoxide 2 from 1 suggests a biogenetic pathway from geraniol/nerol to 3. By comparison, the synthesized 8 exhibits mushroom and celery odor, typical of fractions of the A. salsoloides oil containing 8.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.199219920148
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  • 4
    Digitale Medien
    Digitale Medien
    Terpenes and Terpene Derivatives, XXIX. Synthesis and Olfactive Properties of ( - )- and rac-Silphiperfol-5-en-3-ol and of Some Tris-nor Derivatives (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 669-678 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Artemisia laciniata ; Sesquiterpene alcohols, tricyclic ; Structure-odor correlation ; (R)-(+)-Pulegone ; 1,4-Grignard reaction ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The new sesquiterpene alcohols silphiperfol-5-en-3-ol [( - )-1a] and the corresponding 7-epi compound (+)-1b, important constituents of the essential oil of Artemisia laciniata have been synthesized in 13 steps by starting from (R)-(+)-pulegone (6) in an overall yield of 8%. The key reaction is the coppercatalyzed 1,4-Grignard addition of the iodo acetal 34 to the enone (+)-4 in the presence of TMSCI and TMEDA to give the silyl ether 38. Hydrolysis with spontaneous aldol cyclization and dehydration leads to the silphiperfolenones (+)-2a, b which are separable by flash chromatography. The reduction with L-selectride® gives the alcohols ( - )-1a and (+)-1b which are identical in all physical properties with the isolated natural compound. With LiAlH4 the diastereoisomers 42a, b are formed. Olfactive evaluation of the isomers ( - )-1a and (+)-1b has shown that the odor of the naturally occurring mixture of 1a, b with the descriptors woody, ambergris, slightly camphoraceous is correctly assigned. ( - )-1a represents the more woody and camphoraceous, (+)-1b the more animal facette of ambergris. The odor of rac-1a, b of the diastereoisomers 42a, b and of the ketones (+)-2a, b is also described as well as that of the tris-nor-silphiperfolene derivatives 29-31.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.1992199201114
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  • 5
    Digitale Medien
    Digitale Medien
    Terpenes and Terpene Derivatives, XXVII. Salsolene oxide - A sesquiterpene epoxide with a new carbon skeleton (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 1353-1355 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Essential oil ; Artemisia salsoloides ; Compositae ; Sesquiterpene, new skeleton of ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: From the essential oil of Artemisia salsoloides a sesquiterpene epoxide with a new carbon skeleton, salsolene oxide (1), could be isolated. The structure and relative stereochemistry were deduced from extended NMR studies.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.1991199101232
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