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Abstract:

The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction. © 2008 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
Autor:Maes, D.; Riveiro, M.E.; Shayo, C.; Davio, C.; Debenedetti, S.; De Kimpe, N.
Filiación:Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
Instituto de Biología y Medicina Experimental, Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina
Laboratorio de Radioisótopos, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junin 956, 1113 Buenos Aires, Argentina
Cátedra de Farmacognosia, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Calle 115 y 47, 1900 La Plata, Argentina
Palabras clave:Coumarins; Natural products; Total synthesis; Wittig reaction; 5,7,8 trimethoxycoumarin; artanin; benzaldehyde derivative; coumarin derivative; fraxinol; leptodactylone; unclassified drug; article; chemical structure; priority journal; synthesis; Wittig reaction
Año:2008
Volumen:64
Número:19
Página de inicio:4438
Página de fin:4443
DOI: http://dx.doi.org/10.1016/j.tet.2008.02.059
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v64_n19_p4438_Maes

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Citas:

---------- APA ----------
Maes, D., Riveiro, M.E., Shayo, C., Davio, C., Debenedetti, S. & De Kimpe, N. (2008) . Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins. Tetrahedron, 64(19), 4438-4443.
http://dx.doi.org/10.1016/j.tet.2008.02.059
---------- CHICAGO ----------
Maes, D., Riveiro, M.E., Shayo, C., Davio, C., Debenedetti, S., De Kimpe, N. "Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins" . Tetrahedron 64, no. 19 (2008) : 4438-4443.
http://dx.doi.org/10.1016/j.tet.2008.02.059
---------- MLA ----------
Maes, D., Riveiro, M.E., Shayo, C., Davio, C., Debenedetti, S., De Kimpe, N. "Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins" . Tetrahedron, vol. 64, no. 19, 2008, pp. 4438-4443.
http://dx.doi.org/10.1016/j.tet.2008.02.059
---------- VANCOUVER ----------
Maes, D., Riveiro, M.E., Shayo, C., Davio, C., Debenedetti, S., De Kimpe, N. Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins. Tetrahedron. 2008;64(19):4438-4443.
http://dx.doi.org/10.1016/j.tet.2008.02.059