A Novel Synthesis of Berbines- Condensation of 2-(3,4-Dimethoxyphenyl) Ethyl Bromide with 1,4-Dihydro-6,7-Dimethoxy-3 (2H) Isoquinolone-Synthesis of (+)-Xylopinine |
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Authors: | G. D. Pandey K. P. Tiwari |
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Affiliation: | 1. Department of Chemistry , University of Allahabad , Allahabad, 211 002, India;2. Department of Chemistry , University of Allahabad , Allahabad, 211 002, India;3. Hygiejnisk Institut, Department of Community Health and Environmental Medicine , J. B. Winsl?wsvej 19, D.K., 5000, Odense C, Denmark |
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Abstract: | Recently we reported an efficient synthesis of the berbine alkaloids3,4 by the use of the bromo esters5 prepared from 3-isochromanones. Now a new general synthetic route to the berbine alkaloids beginning with the condensation of the phenethylbromide 3 and 3-(2H) isoquinolone 2 is being described. The method gains added advantage of placing desired substitution on both rings A and D of the berbine, emerging from the easy availability of the starting compounds. In conclusion, the present results have not only added one more efficient example to more than a dozen successful procedures of the berbine synthesis6 but also offer a potential route to the structurally parallel indoloquinolizidine alkaloids. |
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