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Synthesis 2010(1): 91-97
DOI: 10.1055/s-0029-1217047
DOI: 10.1055/s-0029-1217047
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Hydroxyarylketones via Ring-Opening of Lactones with Aryllithium Reagents: An Expedient Synthesis of (±)-Anabasamine
Further Information
Received
1 July 2009
Publication Date:
19 October 2009 (online)
Publication History
Publication Date:
19 October 2009 (online)
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Abstract
The regioselective ring-opening of lactones (δ-valerolactone and γ-butyrolactone) with aryllithium reagents is reported for the construction of a series of δ-hydroxy aryl ketones and γ-hydroxy aryl ketones. Application of this method for the expeditious syntheses of (±)-anabasamine and its nicotine-related analogue are also described.
Key words
ketones - lactones - nucleophilic addition - ring-opening - natural products
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References
New address: S. C. DiMaggio, Department of Chemistry, Xavier University of Louisiana, New Orleans, LA 70118, USA