After obtaining appreciable quantities of 6, we turned our attention to optimizing the envisioned nontemplated, intramolecular vinylogous aldol condensation (reaction at the γ-site). Of note, reaction at the αsite yields the aldol product, which is the major competing pathway. Initial attempts began with in-situ enol formation and intramolecular condensation with TMS-Cl and KO t Bu (Table , Entry 1). While a modest generation of the TMS enol ether was observed, neither the aldol nor vinylogous aldol products were formed. Complete conversion of 6 to the silyl enol ether with the addition of NaI did not result in the desired product (Entry 2). Alternate activation methods involving Storklike reaction conditions using piperidine, pyrrolidine, and pyridine also did not result in either aldol or vinylogous aldol products (shown in SI). We hypothesized additives that could enhance the leaving group ability of water would promote the desired condensation step by facilitating the dehydration. When acetic anhydride was added, we observed the formation of the desired product 7 (Entry 3); however, these conditions were found to be not scalable. Further, the intermolecular reaction was a significant byproduct. As such, we opted to use Burgess Reagent (BR), an intramolecular dehydrating reagent. Although we were able to obtain promising results, we found the yield to be low (Entry 4). By diluting the reaction mixture two-fold, it was possible to suppress unwanted intermolecular coupling. This modification allowed us to increase the yield to a satisfactory 67% (Entry 5). Of note, further dilution of the reaction did not significantly impact the yield. Finally, reactions with indolium 8, benzo[e]indolium 9, or benzo[cd] indolium 10 gave 11 (SiHD-1), 12 (SiHD-2), and 13 (SiHD-3 aka SWIR-HD, vide infra), respectively.