Efficient Synthesis of Thalifoline and Its Analogs

Thalifoline (1) and its analogs were synthesized from methyl 3-hydroxy-4-methoxy benzoate by prenyl etherification, Claisen rearrangement, oxidation, imine formation, reductive amination and intramolecular amidation. The last three steps, imine formation, reductive amination, and intramolecular amid...

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Bibliographic Details
Published in:Synthetic communications 2009-04, Vol.39 (10), p.1752-1758
Main Authors: Li, Qiang, Zhang, San-Qi, Wang, Si-Cen, Zhou, Ming-Zhe
Format: Article
Language:English
Subjects:
Claisen rearrangement
intramolecular amidation
isoquinolinone
one-pot method
thalifoline
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Summary:Thalifoline (1) and its analogs were synthesized from methyl 3-hydroxy-4-methoxy benzoate by prenyl etherification, Claisen rearrangement, oxidation, imine formation, reductive amination and intramolecular amidation. The last three steps, imine formation, reductive amination, and intramolecular amidation, were completed in one pot at room temperature.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910802590894