The total synthesis of (±)-dysidiolide was accomplished with a high level of intramolecular stereo-induction. Methylation of 6-carboethoxy-3-chloro-5-methyl-cyclohex-2-enone provided 33 bearing the 6, 7-trans-dimethyl substitution of the C6–C11 B-ring. Diastereoselective conjugate addition upon enone 34 installed the C11 stereogenic center. Annulation then provided an A-ring enone (23), a substrate for a challenging conjugate ...