The synthesis of 1-1 began with a thermodynamic methylation of 2-methylcyclohexanone (4-4) to produce 4-5 in 79% yield (Scheme 4B). 20 Employing Böhme's salt (4-6), 21 4-5 was converted to 3-3, which was directly subjected to the pyridine synthesis conditions. Treatment of crude 3-3 with known 1,3-diketone 3-2 and NH4OAc resulted in an intermediate dihydropyridine 4-7 after alkylation and successive condensation reactions. Oxidation of 4-7 occurred upon sparging oxygen through the reaction mixture, producing the tricyclic pyridine 4-1 in an unoptimized 16% yield over two steps. Deprotonation of ketone 4-1 with LDA and trapping with 3-furaldehyde (4-3) led to alcohol 4-8 as a 4:1 mixture of diastereomers, which was acetylated in a separate operation to form 4-9 in 51% yield over two steps. An intramolecular acetate aldol reaction was initiated by deprotonation of 4-9 with KOt-Bu, to reveal an intermediate tertiary alcohol 4-10. Subsequent dehydration of the resulting alcohol 4-10 with Burgess reagent gave rise to 3-1 in 36% yield over two steps, which possesses the tetracyclic core of xylogranatopyridine B (1-1). Although the main carboskeleton could be constructed following this approach, the low yielding reaction sequence and linear nature of this strategy rendered it undesirable. Therefore, alternative coupling approaches were pursued to access xylogranatopyridine B (1-1).