Regioselective Synthesis of γ -Butenoildes Mediated by Silvertrifluroacetate with β-Halo Acetals
Author Affiliations
- 1Department of Chemistry, Faculty of Science & Science Education, Kano University of Science & Technology, Wudil, Kano State, NIGERIA
Res. J. Recent Sci., Volume 1, Issue (1), Pages 85-88, January,2 (2012)
Abstract
γ-Butenoildes were prepared by 1,4 addition of β-halo acetals with 2-(tert-butyldimethylsiloxy)-3-methylfuranone mediated by silvertrifluroacetate in one step with high regioselectivity The structures of these products were determined using 1H NMR, 13C NMR, Mass spect. and IR analysis
References
- Ishibashi, M.; Kimihoro, M.; Li, Y. S., Ohizumi, Y. Littoralisone, A Novel Neuritogenic Iridolactone Having an Unprecedented Heptacyclic Skeleton Including Four- and Nine-Membered Rings Consisting of Glucose from Verbena littoralis, Journal of Organic Chemistry, 66, 2165 (2001)
- Macmillan, D. W. C. & Mangion, I. K. Total Synthesis of Brasoside and Littoralisone, Journal of the American Chemical Society, 127, 3697 (2005)
- Makama, B. Y. (2010) Synthesis of an enantioenriched tricyclci iridolactone core in Brasoside, Science World Journal, 5, 15 (2010)
- Larson, G. L. ; Klesse, R. An Improved Synthesis of the Ethylene Acetal of 3-Iodopropanal and The Ethylene Ketal of 4-Iodo-2-butanone, J. Org. Chem., 50, 3627 (1985)
- Oku, A., Kinugasa, M., Kamada, T. Deprotection of Acetals and Silyl Ethers by DDQ. Is DDQ a Neutral Catalyst, Chem. Lett.,22,165 (1993)
- Tanemura, K., Suzuki, T., Horaguchi, T. 2,3-Dichloro-5,6-dicyano--benzoquinone as a mild and efficient catalyst for the deprotection of acetals J. Chem. Soc., Chem, Commun., 979 (1992)
- Perrin, D. D.; Amarego, W. L. F. Purification of Laboratory Chemicals, Pergamon Press Oxford (1998)