Artículo
Antonioletti, R.; Bonadies, F.; Monteagudo, E.S.; Rossi, A.; Scettri, A. "Lipoxygenase-catalyzed dehydration of furylhydroperoxides" (1992) Tetrahedron Letters. 33(14):1919-1920
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Abstract:
3-alkoxycarbonyl-5(1-hydroperoxyalkyl)-furans 1 are changed into the corresponding 5-acyl and 5-formyl derivatives 2 by a lipoxygenase-catalyzed process. The conversion shows to proceed in enantioselective way leading to chiral furylhydroperoxides and furylalcohols. 3-alkoxycarbonyl-5(1-hydroperoxyalkyl)-furans 1 are changed into the corresponding 5-acyl and 5-formyl derivatives 2 by a lipoxygenase-catalyzed process. © 1992.
Registro:
| Documento: | Artículo |
| Título: | Lipoxygenase-catalyzed dehydration of furylhydroperoxides |
| Autor: | Antonioletti, R.; Bonadies, F.; Monteagudo, E.S.; Rossi, A.; Scettri, A. |
| Filiación: | Centro CNR di Studio per la Chimica delle Sostanze Organiche Naturali, Dipartimento di Chimica, Università La Sapienza, P.le A. Moro 5, 00185 Roma, Italy Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Buenos Aires, Argentina |
| Palabras clave: | furan derivative; lipoxygenase; article; enzyme activity; priority journal; reaction analysis; synthesis |
| Año: | 1992 |
| Volumen: | 33 |
| Número: | 14 |
| Página de inicio: | 1919 |
| Página de fin: | 1920 |
| DOI: | http://dx.doi.org/10.1016/S0040-4039(00)74178-5 |
| Título revista: | Tetrahedron Letters |
| Título revista abreviado: | Tetrahedron Lett. |
| ISSN: | 00404039 |
| CODEN: | TELEA |
| CAS: | lipoxygenase, 9027-17-2, 9029-60-1 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v33_n14_p1919_Antonioletti |
Referencias:
- Corey, (1986) Stereochemistry of Organic a Bioorganic Transformations, pp. 1-12. , W. Bartmann, W.B. Sharpless, VCH Publishers
- Teng, Smith, (1976) J. Steroid Biochem., 7, p. 577
- Zhang, Kyler, (1989) J. Am. Chem. Soc., 111, p. 9241
- Dussault, Lee, Kreifels, (1991) J. Org. Chem., 56, p. 4087
- Antonioletti, Bonadies, Florio, Scettri, (1990) Gazz. Chim. It., 120, p. 471
- Frimer, Single oxygen in peroxide chemistry (1983) The chemistry of peroxides, pp. 220-225. , S. Patai, J. Wiley, Chichester
- For ex. 2d; IR(1%, CCl4): 1720, 1690 cm−1. H1-NMR (CDCl3): δ 7.40(s, 1H), 4.28(q, 2H; J=7Hz), 2.62 (s, 3H), 2.42(s, 3H), 1.33(t, 3H; J=7Hz). MS(m/z): 196(M+) 3d; IR (1%, CCl4): 3610-3500, 1720, 1610 cm−1. H1-NMR (CDCl3): δ 6.44(s, 1H), 4.80(1, 1H; J=7Hz), 4.24 (q, 2H; J=7Hz), 2.52(s, 3H), 2.20-1.80 (broad s, 1H), 1.49(d, 3H; J=7Hz), 1.30 (t, 3H; J=7Hz). MS(m/z): 198(M+); The enantiomeric excesses of alcohols 3 have been determined by 1H-NMR analysis in the presence of Eu(hfc)3; Martin, General strategies for the asymmetric synthesis of oxygenated natural products (1988) Natural Products Chemistry III, pp. 135-153. , Atta-ur-Rahman, P.W. LeQuesne, Springer Verlag, Berlin
Citas:
---------- APA ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Rossi, A. & Scettri, A. (1992) . Lipoxygenase-catalyzed dehydration of furylhydroperoxides. Tetrahedron Letters, 33(14), 1919-1920.http://dx.doi.org/10.1016/S0040-4039(00)74178-5
---------- CHICAGO ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Rossi, A., Scettri, A. "Lipoxygenase-catalyzed dehydration of furylhydroperoxides" . Tetrahedron Letters 33, no. 14 (1992) : 1919-1920.http://dx.doi.org/10.1016/S0040-4039(00)74178-5
---------- MLA ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Rossi, A., Scettri, A. "Lipoxygenase-catalyzed dehydration of furylhydroperoxides" . Tetrahedron Letters, vol. 33, no. 14, 1992, pp. 1919-1920.http://dx.doi.org/10.1016/S0040-4039(00)74178-5
---------- VANCOUVER ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Rossi, A., Scettri, A. Lipoxygenase-catalyzed dehydration of furylhydroperoxides. Tetrahedron Lett. 1992;33(14):1919-1920.http://dx.doi.org/10.1016/S0040-4039(00)74178-5
