Total syntheses of (-)-spirooliganones A and B.

The enantioselective syntheses of (-)-spirooliganones A and B have been accomplished in eight steps from commercially available starting materials. Noteworthy transformations include a three-component hetero-Diels-Alder cycloaddition to construct the tetracyclic core of spirooliganones, a Sharpless asymmetric dihydroxylation, and a tandem oxidative dearomatization/cyclization to build the oxa-spiro cyclohexadienone skeleton. The straightforward syntheses were performed without protecting groups.