Eleganine A is a cytotoxic indole alkaloid recently isolated from the leaves of Tabernaemontana elegans. Its unique structure arises from rearrangement of a canonical corynanthe skeleton, resulting in the presence of a 4-ethylidene-3-alkylproline core. Employing a chiron approach, we describe an efficient and scalable synthesis of the proline subunit of eleganine A, as well as efforts toward its proposed structure. ©ARKAT USA, Inc