Our retrosynthetic strategy (Scheme 2) was targeted towards hemiketal 5, an oxocarbenium precursor which could be used to access each lycibarbarine (1-3) by controlled acid-mediated spiroketalisation followed by late-stage formylation. We envisaged 5 could be accessed via an N-alkylation of tetrahydroquinoline 6 with epoxide 7, followed by oxidation. Tetrahydroquinoline 6 could be prepared by the reduction of the commercially available 5-bromo-8-hydroxyquinoline (8). Epoxide 7 would be accessed from 2-deoxy-D-ribose, as this chiral pool material possesses the correct stereochemistry required for 1-3. Synthetic studies began with the construction of epoxide 7as developed for our synthesis of acortatarin A from 2deoxy-D-ribose via sequential Wittig methylenation, protection, and epoxidation. This protocol proceeded in good overall yield on a multi-gram scale (see Supporting Information for full details). Tetrahydroquinoline 6 was accessed in one step from 5bromo-8-hydroxyquinoline ( ) via boric acid-catalysed reduction using the mild organic hydride donor Hantzsch ester (9) (Scheme 3). Alternative hydride sources such as NaBH4, NaBH3CN, HBpin, and B2pin2 proved unreactive towards substrate 8. Aminolysis of epoxide 7 with tetrahydroquinoline 6 afforded alcohol 10 in good yield. However, the proposed oxidation and cyclisation of 10 to hemiketal 5 proved challenging (see Supporting Information for full details). This was likely due to sensitivity of the tetrahydroquinoline moiety to oxidative conditions, in addition to significant degradation of hemiketal 5 taking place during purification. To circumvent the need for oxidation after N-alkylation, epoxide 7 was converted to -bromoketone 11, which would serve as an alternative electrophile for the key C-N coupling. Conversion of epoxide 7 to -bromoketone 11 was