With both fragments (13 and 21) in hand, we began to coax their union in a way that would result in selective 1,6-conjugate addition. Critical to the success of this strategy was the formation of the β,γ-unsaturated isomer 22 rather than the a,bunsaturated congener due to the ensuing asymmetric proton transfer (vide infra). Conventional Cu-mediated conjugate additions showed complete selectivity for 1,6 versus 1,4 addition albeit in low yield (10-46%). This classic approach suffered from a lack of reproducibility and labor-intensive, multi-stage processes that necessitated the usage of tert-butyl lithium in order to affect cupration. Extensive attempts to improve this chemistry (see SI for a summary) ultimately inspired exploration of a more modern solution to this problem which involved investigating various metals to carry out a direct conjugate addition (Pd, Zn, Ti, Cr, Co, etc.). The Nicatalyzed conjugate addition methodology recently reported by Zhou and co-workers was particularly exciting in this regard. Indeed, initial hits with their reported conditions were promising and after a few rounds of optimization (see inset table for brief summary and SI for full optimization) the targeted reaction could be accomplished on gram scale (61% yield) delivering the desired product 22 through concomitant C3-protonation (> 10:1 selectivity). This powerful technology benefits from non-cryogenic temperature, a lack of highly reactive/corrosive materials (organolithium, cyanide, etc.), and its practicality in terms of set-up.