The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene–alkene [2+2] cycloaddition and a late‐stage carboxylic acid directed C(sp3)H oxidation. The synthesis requires only eight steps from norbornadiene.
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Rasik et al. (2014) studied this question.
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