"La hierba de la cucaracha" is an anticockroach/insecticidal powder prepared from the dried leaves of the plant Haplophyton cimicidum which has been used at least since the Aztec era in parts of Mexico and Central America. The pioneering studies of H. R. Snyder and co-workers at the University of Illinois (Urbana-Champaign) led to the isolation and chemical characterization of the active principles, including various dimeric and monomeric indole alkaloids which are chemical relatives of aspidospermine types. However, it remained for the groups of M. P. Cava, P. Yates, and D. E. Zacharias to determine the complex structures of the individual alkaloids including aspidophytine (1) and haplophytine (2). The synthesis of 1 and 2 has remained an unanswered challenge for more than a quarter century, despite remarkable achievements in the area of aspidospermine alkaloid synthesis. We describe herein a short and convergent enantioselective synthesis of aspidophytine (1), the logical first target on the path to the synthesis of haplophytine itself, and an obvious biosynthetic precursor. The construction of 1 entailed the synthesis of two building blocks, the substituted tryptamine 6 and the chiral dialdehyde 11. The totally synthetic 1 was shown to be identical with a sample of naturally produced aspidophytine by comparison of 1H and 13C NMR spectra, IR and mass spectra, optical rotation, mp and mixed mp, and thin layer chromatographic comparison in three different solvent systems.