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  • Terpenes  (3)
  • Essential oil  (2)
  • 5-Hydroxygeranyl derivatives  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Terpenes and terpene derivatives, XXXIII. Synthesis of rac-cis- and -trans-dracunculifoliol and their 10-epimersDedicated to Manfred Schlosser on the occasion of his 60th birthday. (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 231-240 
    Details
    ISSN: 0947-3440
    Keywords: Dracunculifoliol ; Eudesmanes, 8(7→6)-abeo- ; Vassoura oil ; Baccharis dracunculifolia ; Terpenes ; Hydrindane Derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The cis-aldehyde 9, a key intermediate in the total synthesis of cis-dracunculifoliol (1) previously isolated from Vassoura oil, was prepared starting from the bicyclic enone 5 via the nitrile 8. Grignard reaction of 9 led exclusively to epi-1. Oxidation to the ketone 10 followed by reduction gave a separable mixture of the natural isomer 1 and epi-1. - The synthesis of trans-dracunculifoliol (2) starts with the 6-methoxytetralone 14. After some usual steps, the trans-octalin 17 was obtained. MMPP-HIO4 oxidation gave compound 19 which was transformed into the iodo ester 26, precursor of the hydrindane ester 27. Analogously to the synthesis of epi-1 the epi-trans-dracunculifoliol (epi-2) was formed via alcohol 28 and aldehyde 29. Oxidation ( 30) and reduction furnished the natural trans alcohol 2. - Olfactory evaluation of the purified isomers 1, epi-1, 2, and epi-2 showed that all of them possess only a weak, woody odor. Therefore, the dracunculifoliols 1 and 2 are not responsible for the typical earthy, leathery, and spicy odor of the Vassoura oil.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950233
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  • 2
    Electronic Resource
    Electronic Resource
    Cameroonane, Prenopsane and Nopsane, Three New Tricyclic Sesquiterpene Skeletons (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1205-1212 
    Details
    ISSN: 1434-193X
    Keywords: New tricyclic sesquiterpene alcohols ; Natural products ; Essential oil ; Compositae ; Odoriferous substances ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Terpenes and Terpene Derivatives, XXXI. New Bisabolene Derivatives and a Salsolene Ketone from Artemisia sieberi Bess. (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 111-116 
    Details
    ISSN: 0170-2041
    Keywords: Artemisia sieberi ; Terpenes ; Sesquiterpenes ; 1,8-Sesquicineole derivatives ; Bisabolene derivatives Sesquiphellandren-7-ol ; Salsolene ketone ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the essential oil of Artemisia sieberi growing near Tehran some new bisabolene derivatives could be isolated. The structures of (-)-dehydro-1,8-sesquicineole (1), (E)-dehydro-1,8-sesquicineol-12-yl acetate (4), bisabola-2,11-dien-10-one inner 1,7-acetal (14) and salsolene ketone 15 could be established by their 1H- and 13C-NMR spectra. Sesquiphellandren-7-ol (11), a trace constituent of the oil, was identified by a comparison of its 1H-NMR spectrum with that of sesquiphellandren-9-ol (bisacurol).
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930120
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  • 4
    Electronic Resource
    Electronic Resource
    Megastigmanes and Other Constituents of the Absolute of Boronia megastigma from Tasmania (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 1043-1047 
    Details
    ISSN: 0170-2041
    Keywords: Boronia megastigma ; Rutaceae ; Megastigm-7-en-9-ones ; Coumarates ; 5-Hydroxygeranyl derivatives ; 8-Hydroxylinalool derivatives ; N-[2-(4-Prenyloxyphenyl)ethyl] tiglamide ; Odoriferous substances ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Some low-volatile constituents of the absolute of Boronia megastigma (Rutaceae) from Tasmania were isolated and characterized. Besides β-ionone (1) and many of its derivatives, e.g. 2-7, we isolated the isomeric 3-hydroxymegastigm-7-en-9-ones 8-10 and the megastigm-7-ene-3,9-dione (11). Furthermore, the p-coumaric acid derivatives (E, Z)-12 and -13, alkyl esters of 8-hydroxylinalool (16a-g) and the N-[2-(4-prenyloxyphenyl)ethyl]tiglamide (17) were identified.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419941015
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  • 5
    Electronic Resource
    Electronic Resource
    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
    Keywords: Essential oil ; Artemisia salsoloides ; Compositae ; Sesquiterpene, new skeleton of ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101232
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  • 6
    Electronic Resource
    Electronic Resource
    Terpenes and Terpene Derivatives, XXX. Isolation and Synthesis of Isohumbertiol, the First Naturally Occurring Sesquiterpene Alcohol with a Humbertiane Skeleton (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 1325-1328 
    Details
    ISSN: 0170-2041
    Keywords: Isohumbertiol ; Cabreuva oxide ; Vassoura oil ; Baccharis dracunculifolia ; Sesquiterpenes ; Terpenes ; Humbertiol ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From Vassoura oil (Baccharis dracunculifolia DC.) the four isomeric isohumbertiols A-D (7-10), the first naturally occurring sesquiterpene alcohols with a humbertiane skeleton could be isolated and assigned unambiguously by establishing a correlation with the known cabreuva oxides A-D (3-6). Reaction of the ketone (+)-16 with vinylmagnesium bromide gave a mixture of the isohumbertiols B and D [(+)-8 and ent-10]. Treatment of 8/10 with SnCl4 furnished the tetraline derivative 18, whereas with hydrochloric acid the cabreuva oxides B and D (4 and 6) were obtained.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201218
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