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Synthesis 2002(15): 2187-2190
DOI: 10.1055/s-2002-34844
DOI: 10.1055/s-2002-34844
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of Thalifoline
Further Information
Received
11 June 2002
Publication Date:
21 October 2002 (online)
Publication History
Publication Date:
21 October 2002 (online)
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Abstract
An efficient multi-step approach for the synthesis of the isoquinolin-1-one alkaloid thalifoline (1) is described. The key intermediate carbamate 8a underwent a modified Bischler-Napieralski-type cyclization using Banwell’s Tf2O/DMAP conditions to form the lactam 9a under mild conditions and in excellent yield.
Key Words
alkaloids - thalifoline - quinolines - heterocycles - isoquinoline - ring closure - cyclizations
- 1
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References
In ref. [10] J. Finkelstein reported this compound using a different procedure but did not quote a melting point. Sigma-Aldrich lists this compound as having a mp of 61-64 °C.