A unified approach to the daucane and sphenolobane bicyclo[5.3.0]decane core: enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene.

Access to the bicyclo[5.3.0]decane core found in the daucane and sphenolobane terpenoids via a key enone intermediate enables the enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene. Central aspects include a catalytic asymmetric alkylation followed by a ring contraction and ring-closing metathesis to generate the five- and seven-membered rings, respectively.