Snider's impressive synthesis of isosteviol relied on their pioneering oxidative radical cascade methodology from polyene 10-prepared in 10-steps (LLS) with 2 FGI's and 3 redox manipulations. Our initial attempts using more traditional organometallic cross-coupling chemistry (Figure ) yielded no success in the first coupling (see SI, Figure ). Using vinyl organolithium reagents led to a retro-lithium ene to expel allyl lithium and treating the allyl vinyl iodide 17 with organometallic reagents led to recovery of vinyl iodide. The only conditions identified capable of forging the desired bond between the acid 18 and skipped diene 17 were the developed electrochemical conditions, which gratifyingly gave the desired product acid 19 in 53% isolated yield on gram-scale. The resulting acid 19 was activated and coupled to vinyl iodide 20 bearing the reactive β-ketoester functionality (a testament to the functional group compatibility of the developed conditions) providing more than a gram of polyene 10 in 6 steps LLS.