Efforts toward the total synthesis of (±)-toxicodenane A utilizing an oxidopyrylium-based [5+2] cycloaddition of a silicon-tethered BOC-pyranone

[Display omitted] •Synthetic efforts toward the tricyclic core of (±)-toxicodenane A are reported.•Feist-Benary, Achmatowicz, Boc-protection used to construct precursor.•Oxidopyrylium-based [5+2] cycloaddition of Boc-pyranone-vinyl silane. Synthetic efforts toward the tricyclic core of (±)-toxicodenane A are reported. This strategy takes advantage of the Feist-Benary furan annulation, Achmatowicz oxidative rearrangement, and oxidopyrylium-based [5+2] cycloaddition to access a key tetracyclic intermediate. This work provides a foundation that can be utilized toward the total synthesis of the natural product.