Solid Phase Synthesis of 17α-E/Z-(X-Phenyl)-Vinyl Estradiols Using the Stille Coupling Reaction

As a continuation of our program to develop probes for the hormone binding domain (HBD) of the estrogen receptor (ER), we designed a series of novel 17α-E/Z-(X-phenyl)-vinyl estradiols. Based upon our experience with solution chemistry we applied solid phase synthesis using carboxylated resins to synthesize the new compounds. The Stille coupling reaction permitted the introduction of a variety of functional groups and positional isomers on the terminal phenyl group. Subsequent cleavage from the resin generated a series of novel estradiol derivatives.