Tunable enzymatic catalysts for C-H oxidation represent perhaps the best and most cost-effective solution to stereo-and regio-controlled preparation of high-value hydroxylated building blocks for organic synthesis. The downstream functionalization of such intermediates has historically relied exclusively on polar bond disconnections thereby diminishing the strategic benefit incurred by their rapid access. By leveraging the power of radical retrosynthesis with biocatalysis incredibly concise and modular pathways to complex three-dimensional architectures are now within reach.