Methods that enable easy access to functionalized furans are of great current interest due to the presence of such units in a number of natural products, pharmaceuticals and agrochemicals. The discovery and scope of an unprecedented, ring-degenerate rearrangement of 3-acyl-2-alkoxyfurans 1 to 2-alkyl-3-carboalkoxyfurans 2 will be described. Substrates 1 are conveniently prepared in a single step by “click-unclick” oxazole-ynone [4+2]-cycloaddition/cycloreversion. The scaffolding power of this chemistry will be demonstrated by the first synthesis of pumiloxide aldehyde (PA), a rare labdane furfural isolated from the seeds of the Cameroonian medicinal tree Turreanthus africanus.

Unusual rearrangement of 3-acyl-2-alkoxyfurans enabling appendage of a carbon substituent at C-2: Application to the synthesis of furanolabdanes

249th National Meeting (2015)

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