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A series of highly functionalised γ-hydroxyacryl γ-hydroxybutenolides, 2, were synthesised in 25–50% overall yields in two or three steps from 2-furfural using a tandem Baylis–Hillman-singlet oxygen oxidation reaction.

The scope and limitations of a regioselective synthesis of either alpha- or beta-substituted gamma-hydroxybutenolides from 3-furfural and enones are described. The sequence features a Baylis-Hillman reaction followed by singlet oxygen oxidation with use of either an amine base or TBAF as the regioselectivity switches. Structural studies in solution on some of the resulting gamma-hydroxybutenolides are also reported.

A series of highly functionalised γ-hydroxyacryl γ-hydroxybutenolides, 2, were synthesised in 25–50% overall yields in two or three steps from 2-furfural using a tandem Baylis–Hillman-singlet oxygen oxidation reaction.

A facile synthesis of alpha-substituted gamma-hydroxybutenolides from 3-furfural was achieved using a Baylis-Hillman reaction followed by singlet oxygen oxidation. The regioselectivity of this conversion was controlled by using TBAF.

A facile synthesis of beta-functionalized gamma-hydroxybutenolides was achieved using a Baylis-Hillman reaction followed by singlet oxygen oxidation. The conversion from 3-furfural was regio- and diastereoselective. [reaction: see text].