The limonoid natural products are a diverse family of terpenoids characterized by their structurally conserved C17-furan and various modes of skeletal rearrangements. A fascinating sub-family of these natural products, the limonoid alkaloids, are recently isolated from the Chinese mangrove, Xylocarpus granatum. The structural hallmark of the limonoid alkaloids is the tetrasubstituted pyridine embedded in the core structure (Scheme 1), as typified by xylogranatopyridine B (1-1) and granatumine A (1-2). Furthermore, granatumine A (1-2) is a member of the bislactone limonoid alkaloids, in which the Aring has undergone further modification to form a 5-membered lactone ring fused to the 6-membered ring adjacent to the pyridine. For the limited number of bislactone limonoid alkaloids that have been isolated, diversity mainly arises from the oxygen-containing substituents present on the C3 position (1-2 to 1-4), as depicted in Scheme 1. While the C3-methoxy group was assigned as the β-epimer for granatumine A (1-2), several other alkaloids in this class were proposed to have an α-C3-substituent, such as the case of xylogranatin F (1-3). Surprisingly, granatoine (1-4) was proposed to have the same scaffold as xylogranatin F (1-3), except being diastereomeric at the C3, C5, and C10 positions. Traditional methods for pyridine synthesis, including Hantzsch 5 and Chichibabin 6 pyridine synthesis, involve amine condensation onto carbonyl compounds, which entails intrinsic restrictions on the substitution patterns of the target pyridines. More recently, there have been numerous methodological advancements in the synthesis of highly substituted pyridines, many of which utilize transition-metal catalyzed crosscoupling. However, these methodologies have rarely been tested in the realm of complex molecule synthesis. These limonoid alkaloid natural products inspired a compelling question: what are the most effective ways to use ring synthesis as a tool for convergence in the context of such highly substituted pyridines?