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The centenarian Tröger’s base (TB) was envisaged as scaffold for the construction of tubular-shaped cleft molecules due to its the remarkable structural properties. This endeavor started with the synthesis of the three possible diastereomers of a linear symmetrically fused tris-TB analogue, the anti-anti, the syn-syn, and the syn-anti. All three diastereomers showed unprecedented stability to acid
