An unexpected rearrangement of the benzofurobenzazepine skeleton of galanthamine-type alkaloids |
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Authors: | Klá ra Herke,Zsuzsanna Sá nta,Viktor Há da,Gyö rgy Kalaus |
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Affiliation: | a Department of Organic Chemistry and Technology, University of Technology and Economics, H-1111 Budapest, Szt. Gellért tér 4., Hungary b Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, H-1111 Budapest, Szt. Gellért tér 4., Hungary c Spectroscopic Research Division, Gedeon Richter Plc., H-1475 Budapest 10, PO Box 27, Hungary |
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Abstract: | Attempted cyclisation of N-methylated spiro benzazepine-cyclohexenone (5) into the corresponding N-methyl tetracyclic unit of galanthamine-type alkaloids (6) instead gave an unexpected rearrangement to yield a cyclopentanoisoquinolinone derivative (7). Methylation of the tetrahydrobenzofurobenzazepine tetracycle resulted in the expected N-methyl derivative 6, and the anomalous product 8, with structure similar to that of 7. |
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Keywords: | Amaryllidaceae alkaloids Spirocyclohexenone Rearrangement Cyclopentanoisoquinolinone |
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