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A new, stereoselective formal synthesis of hirsutic acid and medium ring carbocyclic systems from salicyl alcohol is described. Cycloaddition between electron deficient partners such as cyclohexa-2,4-dienone and methylmethacrylate, triplet sensitized 1,2-acyl shift and ring-closing metathesis are the key features of our approach.
Formal syntheses of hirsutic acid C and complicatic acid via cycloaddition of cyclohexa-2,4-dienone with methyl methacrylate and a triplet sensitized 1,2-acyl shift are described. The X-ray crystal structure of one of the key intermediates is also reported.
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