Abstract
Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R(2) = R(3) = CO2Me) instead form furans as the major product.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Bridged Bicyclo Compounds, Heterocyclic / chemistry*
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Furans / chemical synthesis*
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Furans / chemistry
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Mesylates / chemistry*
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Molecular Structure
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Tropolone / analogs & derivatives
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Tropolone / chemistry
Substances
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3-methoxy-8-oxabicyclo(3.2.1)octa-3,6-dien-2-one
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Bridged Bicyclo Compounds, Heterocyclic
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Furans
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Mesylates
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2-methoxytropolone
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Tropolone
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trifluoromethanesulfonic acid