Quinoline-containing tethers 11a-c were prepared straightforwardly though standard heterocyclic synthesis as shown in Scheme 2. While compound 10a was commercially available, quinoline aldehydes 10b and 10c were prepared in moderate yield via Skraup synthesis followed by a benzylic oxidation with selenium dioxide. All three aldehydes then underwent an efficient Grignard addition/acetylation sequence to yield the desired tethers 11. All syntheses proved to be relatively scalable, enabling gram quantities to be formed in some cases. Routes to tether 15 were made somewhat more challenging by the need for the construction of a geminally-substituted alkene. While various less modular, multi-step approaches appeared possible, we observed that Kutsumura et al. recently reported 14 a one-pot bromination/cross-coupling strategy to enable the synthesis of 2-aryl substituted allylic alcohol derivatives. Such an approach would enable late-stage variation of the quinoline unit by introducing it in the penultimate cross-coupling step and would further lead to a short and efficient overall synthesis. We therefore prepared 4-methoxybenzyl (PMB)-protected allylic ether 12a. Bromination and cross-coupling proceeded as reported, furnishing the PMB-protected quinoline 14a in reasonable yield (Scheme 3). However, PMB deprotection proved troublesome, leading to either full recovery of the starting material or complete degradation. We therefore considered different protecting groups and after some experimentation found that tetrahydropyranyl (THP) worked efficiently. While a one-pot bromination/cross-coupling approach also proved possible in this case, isolation of bromide 13b gave improved results in the subsequent cross-coupling, with quinoline 14b being isolated in good yield with a reaction that could be scaled to 1 g. Deprotection proved straightforward under standard acidic hydrolysis conditions, and acetylation yielded the desired tether 15b in good yield.