Chemical F/J-Interconversion in the Prostaglandin Family: From Cloprostenol to Its Δ12 -J2 and 15-Deoxy-Δ12,14 -J2 Derivatives

摘要

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 PGJ2 was converted to the target ω-aryloxy derivatives ~12 -PGJ2, its 13Z isomer, and ~12,14 -PGJ2 by hydrol- ysis of the TBDMS protective group. The anticancer activity of some of the synthesized compounds was studied.