Features of Pd-catalyzed reactions of allylic acetates elimination in racemic cloprostenol methyl ester triacetate and 15-acetate of methyl ester 11-deoxyprostaglandin E1

An exclusively stereoselective reaction of AcOH elimination in the title acetate of cloprostenol was described, which led with high yield under Pd(PPh3)4-NaH-THF catalysis to the corresponding 13E,15Z-derivative. In contrast, under the same conditions, the use of methyl ester of 15-acetate 11-deoxyprostaglandin E1 results in regioisomeric reductive elimination products. [Display omitted] •The reaction of prostaglandin with NaH in the presence of a Pd catalyst was target.•Relationships between configuration and energy of unsaturated alcohols were shown.•The structures were optimized by quantum chemical modeling methods.•Elimination products and reductive elimination products were obtained.•The structure of the obtained compounds was thoroughly determined by NMR.