Abstract The β 1-adrenergic antagonist (S, R, R, R)-α, α′-iminobis (methylene) bis (6-fluoro- 3H, 4H-dihydro-2H-1-benzopyran-2-methanol) was synthesized from natural chiral pool starting materials through an efficient, convergent synthetic strategy. The cyclization mechanism of the key step was investigated using computer modeling and is discussed.