Abstract Racemic cloprostenol methyl ester was converted via cyclic 9,11‐phenylboronate esters to 9α,11α‐dihydroxy‐15α‐siloxy (OTBDPS, OTBDMS) derivatives. TES‐Morf selectively reacts with last compounds to exclusively give 11‐TES derivative. In the course of further transformations, the J‐type PG was obtained. The optimal conditions for the 13,14‐double bond shift in the latter were determined and ▵ 12 derivatives were obtained. 15‐TBDMS derivative PGJ 2 was converted to the target ω‐aryloxy derivatives ▵ 12 ‐PGJ 2 , its 13Z isomer, and ▵ 12,14 ‐PGJ 2 by hydrolysis of the TBDMS protective group. The anticancer activity of some of the synthesized compounds was studied.