An Efficient Synthesis of Thalifoline

You-Chu  Wang; Paris E.  Georghiou

doi:10.1055/s-2002-34844

PAPER

An Efficient Synthesis of Thalifoline

You-Chu Wang, Paris E. Georghiou*
Chemistry Department, Memorial University of Newfoundland, St. John’s, Newfoundland and Labrador, A1B 3X7, Canada
e-Mail: parisg@mun.ca;

Abstract

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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

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References

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