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Synlett 2004(7): 1243-1246
DOI: 10.1055/s-2004-825596
DOI: 10.1055/s-2004-825596
LETTER
© Georg Thieme Verlag Stuttgart · New York
DBU-Induced Phenol-Keto Resonance in 3,5-Dihydroxyphthalide: Regioselectivities in Condensations with α,β-Unsaturated Aldehydes - Facile Synthesis of Bioactive Natural and Unnatural Benzopyrans [1]
Further Information
Received
12 February 2004
Publication Date:
10 May 2004 (online)
Publication History
Publication Date:
10 May 2004 (online)
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Abstract
Remarkably tuned regioselectivities are obtained in the condensation of 3,5-dihydroxyphthalide (1) with several α,β-unsaturated aldehydes using DBU and neutral conditions. The linear (65-81%) and angular (51-60%) bioactive natural and unnatural benzopyran derivatives are produced exclusively in one step and are described via phenol-keto resonance.
Key words
3,5-dihydroxyphthalide - phenol-keto resonance - regioselective condensation - α,β-unsaturated aldehydes - benzopyran synthesis
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8Upon silica gel column chromatographic purification of 3, only 1 was eluted from the column. Neutral alumina column purification gave only DBU.