Our goal is to develop a general method to control reactivity in the organic solid state. We aim to achieve this goal by utilizing hydrogen bond donor templates (e.g. resorcinol) to preorganize olefins, attached to pyridines, in positions for stereo- and regiocontrolled [2 + 2] photodimerizations. This goal is being realized through the construction of a variety of molecules (e.g. cyclophanes, ladderanes). Another way in which we believe that the generality of this approach can be realized is through post-synthetic modification of the products. The focus of this presentation is to show how the stereochemistry of products from our template-controlled solid-state reactions is retained upon conversion of 4-pyridyl groups to N-oxides. We will demonstrate how our model system, specifically, rctt-tetrakis(4-pyridyl)cyclobutane, was used to guide the synthesis of rctt-tetrakis(N-oxo-4-pyridyl-[5]-ladderane). Being able to modify products of solid-state reactions represents a next step in utilizing the solid-state as a viable medium in synthetic organic chemistry. Evidence for these transformations will be provided using ¹H NMR spectroscopy and single-crystal X-ray diffraction. The relationship of our post-synthetic strategy to the synthesis of naturally-occurring ladderanes will also be discussed.