We report progress towards the synthesis of a series of chiral conformationally constrained diarylether cyclophanes with varying carbon tether lengths. These cyclophanes are chiral due to the restriction of bond rotation and not by the presence of stereocenters. Cyclophane strucutres are found in naturally occurring compounds and experience conformational constraint due to the presence of a carbon tether connecting the meta and para positions of two aromatic rings. We report several attempted methods for the synthesis of diarylether cyclophanes with varying tether lengths to determine the relationship between tether length and the barrier of racemization. Due to the structural similarities to biologically active diarylether heptanoids, the synthesis of new diarylether cylcophanes could lead to novel compounds with significant biological activity.

Synthesis of chiral conformationally constrained diarylether cyclophanes

253rd National Meeting (2017)

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