Scheme 1 presents the realization of these plans resulting in the first total synthesis of dragocins A-C (1A-1C). A scalable and enantiocontrolled route to the linchpin pyrrolidine 8 was required to evaluate both approaches. Historically, the routes to similar structures are either over 10 steps or are plagued with exhaustive functional group interconversions. 7 As such, distinct strategies were evaluated (see SI for details), all of which failed due to stereochemical challenges, protecting group complications, or time-consuming sequences. A simple and direct stereoselective five-step route to 8 was devised starting from D-tyrosine-derived alcohol 3 (two steps from commercial). Thus, annulation of the corresponding aldehyde (TEMPO, NaOCl, used crude) with triphenylvinylphosphonium bromide 8 delivered dihydropyrrole 4 in 68% yield (94% ee). Subsequent Ts- removal was accomplished using metal-free electrochemical Birch conditions enabled by rapid alternating polarity 9 (rAP, 50% yield). These rAP-based conditions for Ts-amide deprotection are without precedent and represent a safer alternative to conventional Li-naphthalide (which was employed for scaleup before rAP conditions were developed, see SI). This also constitutes the first use of the rAP waveform in total synthesis. Subsequent Brønsted acid-assisted diastereoselective epoxidation of 5 (62% 6, 4.5:1 crude dr) proved superior to epoxidation of 4 which led to a ca. 1:1 inseparable mixture of epoxide diastereomers in low conversion. Undesired diastereomer 7 was separable at this point, which set the stage for a free amine-assisted Lewis-acid mediated epoxide opening of 6 to furnish the key pyrrolidine 8 after in situ Moc protection (78% yield, 4.5:1 rr, gram-scale).