Synthesis and receptor binding affinity of conformationally restricted retinoic acid analogues

In an effort to synthesize two conformationally restricted retinoids utilizing a cyclopropyl ring as bioisostere for the C9–C10 double bond, we describe the synthetic strategies and retinoid receptor binding affinity of the trans-cyclopropyl analogue and the unexpected epimerization of the cis-cyclopropyl analogue.