Synthetic Studies of Biomimetic Diels–Alder Processes toward the Helicterin Family of Natural Products

Although the 2.2.2]-bicyclooctene core of the helicterin, helisorin, and helisterculin class of neolignan natural products could conceivably arise in Nature via Diels–Alder reactions, synthetic explorations have revealed that only under very non-biomimetic conditions can such cycloadditions be performed. In this article, we provide a personal account of explorations towards this natural product family, sharing some additional unpublished synthetic work to test the viability of an alternate, Diels–Alder-based, biogenetic hypothesis for the generation of this unique collection of secondary metabolites.