With the requisite dienone in hand, we could explore triflation and cross coupling with an appropriate twocarbon nucleophile to install the methyl acetate fragment present in 1. Following precedent from Liang's synthetic studies toward meliacarpinin, we were able to deprotonate the B-ring dienone and quench with Comin's reagent to provide dienol triflate 18 in excellent yield. Engaging this sterically hindered triflate in transition metal-mediated cross coupling proved difficult. Precedented cross coupling of a TMS silyl ketene acetal reported by Tiefenbacher and Stoltz 33 provided a starting point (LiOAc, Pd(PPh3)4, THF, 60 °C), but low conversion was observed upon scaleup. As a result, we switched to the more stable TBS silyl ketene acetal 19, and toluene as solvent. These changes allowed us to increase the temperature of the reaction to 90 °C. This, in combination with CsOAc as a more soluble base, provided diene 20 in good yield with excellent reproducibility, even on scales up to two grams. We could then regio-and diastereoselectively epoxidize the B-ring diene from the bottom face with dimethyldioxirane (DMDO) to provide vinyl epoxide 10. This epoxide was the requisite starting material for an etherification reaction with alcohol 9.