Synthesis of a Key Intermediate for the Synthesis of Pyranocoumarins. Contrasting Reactivity in the 1,2-and 1,4-Reduction of an Unsaturated Carbonyl System

Lucian Boldea Department of Chemistry, University of Florida, Gainesville, FL, 32611, U.S.A

Patricia Q. Bottari Department of Chemistry, University of Florida, Gainesville, FL, 32611, U.S.A

Merle A. Battiste Department of Chemistry, University of Florida, Gainesville, FL, 32611, U.S.A

Abstract

[2,2-dimethyl-4-(t-butyldimethylsiloxy)-3,4-dihydro-2H-pyran-6-yl] methanal (1) was synthesized from commercially available butopyronoxyl (2). The selectivity of reducing agents such as DIBAL-H and LiAlH₄ towards butopyronoxyl was studied. Solvent effects were found to influence 1,2 versus 1,4 reduction.

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Synthesis of a Key Intermediate for the Synthesis of Pyranocoumarins. Contrasting Reactivity in the 1,2-and 1,4-Reduction of an Unsaturated Carbonyl System

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Synthesis of a Key Intermediate for the Synthesis of Pyranocoumarins. Contrasting Reactivity in the 1,2-and 1,4-Reduction of an Unsaturated Carbonyl System

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