The requisite vinyl epoxide 10 could be accessed from diketone 11 through coupling and triflation followed by epoxidation of the less hindered B-ring olefin. Then oxidation transforms at C1 and C28 would deliver diol 12. This simplified decalin was envisioned to arise from a Heck cyclization to close the A-ring, set the C4 quaternary stereocenter, and install a functional handle at C28. This ultimately traced back to α-methyl-(R)-carvone (13) which served as a readily available chiral-pool starting material.