Secondary metabolites containing more than eight atoms in a skeletal ring have captured the imagination of synthetic organic chemists for nearly a century. Among ring systems containing eight or more atoms, medium-sized (eight to eleven atoms) rings are regarded as the most difficult to access due to entropic and enthalpic barriers. 5 Consequently, embarking on the syntheses of such complex structures requires careful consideration of route choreography, strategy, and tactics for success. Practitioners engaging in such pursuits have few available general strategies for such ring formations: ring-expansion, ring-contraction, and direct cyclization of the acyclic precursors. However, reduction of these strategies to practice is often not straightforward.