Journal
TETRAHEDRON LETTERS
Volume 51, Issue 52, Pages 6932-6934Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.158
Keywords
Amaryllidaceae alkaloids; Spirocyclohexenone; Rearrangement; Cyclopentanoisoquinolinone
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Funding
- OTKA [K 68734]
- Gedeon Richter Plc
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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