Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate

Studies on the synthesis of racemic tragoponol are described. The western resorcylate unit of tragoponol was efficiently constructed from appropriate diketo-dioxinone and secondary alcohol intermediates using a ketene generation-trapping and aromatization sequence. Further functionalization provided an advanced diketo-dioxinone intermediate which upon desilylation resulted in the formation of a dihydroisocoumarin.