Liebeskind Pyridine Synthesis. Our revised retrosynthetic analysis began with structural simplification of the A-ring to access the key tetracyclic intermediate (3-1), as described in Scheme 6A. As an alternative to the initial construction of the C8-C30 bond, formation the crucial N-C9 bond of the pyridine at an early stage might be advantageous (Scheme 6A). The central ring of 1-1 could be assembled via a modified Liebeskind pyridine synthesis, which entails a Chan-Lam-type cross-coupling with an achiral oxime such as 3-7, and a stannane fragment such as 3-6, 7c to construct the N-C9 bond first, followed by an oxidative 6π-electrocyclization to subsequently form the C8-C30 connection. The less precedented stannane 3-6 was eventually chosen as the coupling partner in the Chan-Lam-type coupling, rather than the typical boronic acid coupling partner, due to its relative ease of preparation and stability.