Abstract:
The fusion of the bicyclo[8.1.0]undecane system in the unique sesquiterpene diketone integrifolian-1,5-dione was found to be cis by X-ray analysis. A revised structure was derived for 'africanone' after reconsideration of the mass spectral data. The revised structure is based on a novel sesquiterpene skeleton and was confirmed by a biomimetic synthesis from integrifolian-1,5-dione. © 1991.
Registro:
Documento: |
Artículo
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Título: | Integrifolian-1,5-dione and a revised structure for 'africanone', biogenetically related sesquiterpene ketones from Lippia integrifolia |
Autor: | Catalán, C.A.N.; de Fenik, I.J.S.; Dartayet, G.H.; Gros, E.G. |
Filiación: | Instituto de Química Orgánica, Facultad de Bioquímica-Química-Farmacia, Universidad Nacional de Tucumán, Ayacucho 491, 4000 Tucumán, Argentina Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
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Palabras clave: | Lippia integrifolia; sesquiterpene ketones; stereochemistry; structure; Verbenaceae; X-ray analysis. |
Año: | 1991
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Volumen: | 30
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Número: | 4
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Página de inicio: | 1323
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Página de fin: | 1326
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DOI: |
http://dx.doi.org/10.1016/S0031-9422(00)95227-0 |
Título revista: | Phytochemistry
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Título revista abreviado: | Phytochemistry
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ISSN: | 00319422
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CODEN: | PYTCA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v30_n4_p1323_Catalan |
Referencias:
- Catalán, de, Retamar, Iturraspe, Dartayet, Gros, (1983) Phytochemistry, 22, p. 1507
- Bohlmann, Zdero, King, Robinson, (1982) Phytochemistry, 21, p. 147
- Matsuo, Nozaki, Nakayama, Kushi, Hayashi, Komori, Kamijo, (+)-Bicyclohumulenone, a novel sesquiterpene ketone of the humulane group from Plagiochila acanthophylla subsp. japonica(liverwort): X-ray crystal and molecular structure of the p-bromobenzoate derivative (1979) Journal of the Chemical Society, Chemical Communications, p. 174
- Shirahama, Osawa, Matsumoto, (1980) J. Am. Chem. Soc., 102, p. 3208
- Dartayet, Catalán, Retamar, Gros, (1984) Phytochemistry, 23, p. 688
- Retamar, Delfini, Iturraspe, (1981) Essenze Deriv. Agrum., 51, p. 40
Citas:
---------- APA ----------
Catalán, C.A.N., de Fenik, I.J.S., Dartayet, G.H. & Gros, E.G.
(1991)
. Integrifolian-1,5-dione and a revised structure for 'africanone', biogenetically related sesquiterpene ketones from Lippia integrifolia. Phytochemistry, 30(4), 1323-1326.
http://dx.doi.org/10.1016/S0031-9422(00)95227-0---------- CHICAGO ----------
Catalán, C.A.N., de Fenik, I.J.S., Dartayet, G.H., Gros, E.G.
"Integrifolian-1,5-dione and a revised structure for 'africanone', biogenetically related sesquiterpene ketones from Lippia integrifolia"
. Phytochemistry 30, no. 4
(1991) : 1323-1326.
http://dx.doi.org/10.1016/S0031-9422(00)95227-0---------- MLA ----------
Catalán, C.A.N., de Fenik, I.J.S., Dartayet, G.H., Gros, E.G.
"Integrifolian-1,5-dione and a revised structure for 'africanone', biogenetically related sesquiterpene ketones from Lippia integrifolia"
. Phytochemistry, vol. 30, no. 4, 1991, pp. 1323-1326.
http://dx.doi.org/10.1016/S0031-9422(00)95227-0---------- VANCOUVER ----------
Catalán, C.A.N., de Fenik, I.J.S., Dartayet, G.H., Gros, E.G. Integrifolian-1,5-dione and a revised structure for 'africanone', biogenetically related sesquiterpene ketones from Lippia integrifolia. Phytochemistry. 1991;30(4):1323-1326.
http://dx.doi.org/10.1016/S0031-9422(00)95227-0