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Abstract:

Two diastereomeric furanones, (4S,5S)-5-(4′-methhyl-3′-pentenyl)-4-hydroxy-5 -methyldihydrofuran-2-one 1 and (4S,5R)-5-(4′-methyl-3′-pentenyl)-4-hydroxy -5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochimistries 1 and 2 were ascertained from NOESY NMR data. Comparison between experimental and calculated 1H-1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher's method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum. © 2001 Elsevier Science Ltd.

Registro:

Documento: Artículo
Título:Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis
Autor:Viturro, C.I.; Maier, M.S.; Stortz, C.A.; De la Fuente, J.R.
Filiación:Facultad de Ingeniería, Universidad Nacional de Jujuy, Gorriti 237, 4600 S. S. de Jujuy, Jujuy, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Facultad de Ciencias Exactas, Universidad Nacional de Salta, Buenos Aires 177, 4400 Salta, Salta, Argentina
Palabras clave:5 (4' methyl 3' pentenyl) 4 hydroxy 5 methyldihydrofuran 2 one; furanone derivative; unclassified drug; antifungal activity; article; Cladosporium cucumerinum; conformation; diastereoisomer; molecular model; mutisia friesiana; nuclear Overhauser effect; priority journal; stereochemistry; structure analysis
Año:2001
Volumen:12
Número:7
Página de inicio:991
Página de fin:998
DOI: http://dx.doi.org/10.1016/S0957-4166(01)00163-X
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v12_n7_p991_Viturro

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Citas:

---------- APA ----------
Viturro, C.I., Maier, M.S., Stortz, C.A. & De la Fuente, J.R. (2001) . Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis. Tetrahedron Asymmetry, 12(7), 991-998.
http://dx.doi.org/10.1016/S0957-4166(01)00163-X
---------- CHICAGO ----------
Viturro, C.I., Maier, M.S., Stortz, C.A., De la Fuente, J.R. "Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis" . Tetrahedron Asymmetry 12, no. 7 (2001) : 991-998.
http://dx.doi.org/10.1016/S0957-4166(01)00163-X
---------- MLA ----------
Viturro, C.I., Maier, M.S., Stortz, C.A., De la Fuente, J.R. "Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis" . Tetrahedron Asymmetry, vol. 12, no. 7, 2001, pp. 991-998.
http://dx.doi.org/10.1016/S0957-4166(01)00163-X
---------- VANCOUVER ----------
Viturro, C.I., Maier, M.S., Stortz, C.A., De la Fuente, J.R. Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis. Tetrahedron Asymmetry. 2001;12(7):991-998.
http://dx.doi.org/10.1016/S0957-4166(01)00163-X