The synthesis described here was enabled by user-friendly reactions and strategies that are inexpensive and scalable. The early stages of this synthetic route focused primarily on the short steps, decagram-scale synthesis of the key intermediate, the pentacyclic compound 12. In the process, a 3-step synthesis of the tetracyclic compound 8 without protecting groups was achieved. In addition, a direct radical coupling of ketone 9 with Mn(OAc)3 was discovered and a decagram-scale synthesis of pentacyclic compound 12, a key intermediate for many vobasine alkaloids, was achieved in only 6 steps. Finally, we developed an efficient bioinspired method for introducing tryptamine, which has a pyrraline structure that is relatively rare in natural products and achieved the first total synthesis and gram-scale supply of pyrrovobasine (1). This methodology is anticipated to be useful for future investigations into the biological activity and structureactivity relationships of pyrrovobasine (1).