Abstract
The Elueocarpus densiflorus indole alkaloid (±)-elaeocarpidine (1) is synthesized in five steps and 31% yield from the commercially available materials 2-(2-bromoethyl)-1,3-dioxolane, ethyl 4-brmobutyrate, and tryptamine hydrochloride (7). The key step is a diisobutylaluminum hydride reductive cyclization of amine lactam 8 to give 1 in 86% yield.