To generate a robust FL or PA signal in vivo, a sufficient amount of incident light must be able to reach a given optical absorber. However, as photons pass through tissue, endogenous pigments (e.g., hemoglobin) can readily intercept and scatter light. A shift toward the SWIR imaging window where interference is minimized promises to enable access to deeper regions of the body. To facilitate this, we designed an efficient synthetic route to access SWIR-HD, in six-steps starting from readily accessible acetal precursors. Typically, Lewis acid catalysts are employed to shift the reactivity preference from the -site to the -site. However, in our case we were able to access compound 7, which is a key intermediate in our synthesis through a non-templated vinylogous aldol reaction. Beyond strategically selecting the base, varying the solvent polarity, and controlling the reaction molarity, we discovered it was essential to include Burgess Reagent to facilitate a key intramolecular cyclization-dehydration sequence. The ability to substitute the endocyclic oxygen atom of the parent HD with an electron-deficient SiMe2 group and vary the donor in the final step using this chemistry was instrumental in red shifting the λabs by 264 nm from 724 nm to 988 nm.