We questioned whether a new entry to the Strychnos family might be designed that could meet the stringent demands of contemporary synthetic chemistry. We envisioned a modular strategy that would enable the enantioselective construction of the Strychnos core in a handful of steps, and therefore access multiple natural products in a scalable and procedurally straightforward manner whilst also minimising the generation of undesirable waste byproducts. In considering possible approaches, we recognised that the indoline core of the alkaloids is an attractive motif for ring formation via cycloaddition, in which an indole precursor would serve as an electron-rich 2p component. This concept has been exploited by Vanderwal (via formal inverse-electron demand Diels-Alder (IEDDA) cycloadditions with tethered Zincke aldehydes, Fig. ) , and also the Boger and Padwa groups (via (3+2) cycloadditions with tethered carbonyl ylides) ; Padwa et al. also reported a (4+2) cycloaddition using a tethered aminofuran in a racemic synthesis of strychnine 18 . However, these elegant strategies also suffer from drawbacks, such as the need for prolonged heating when employing aromatic cycloaddition partners (i.e. furans, oxadiazoles), or the use of diazo compounds and transition metal catalysts (for carbonyl ylide synthesis), or in affording racemic natural products.