Fluoroprostaglandins: Totl Synthesis of (+)-13-Fluoroprostaglandin F2α Methyl Ester

Article abstract of DOI:10.1021/jo00217a019

(+)-13-Fluoroprostaglandin F_2α methyl ester (1) was prepared from the readily available methyl (-)-(1α,4α,5α,7S*)-5-bromospiroheptane-2,2'-<1,3>dioxolane>carboxylate (6).Construction of the 13-fluoro olefinic structural unit was achieved via a Schlosser-Wittig reaction employing chiral aldehyde 2 and chiral ylide 3. (+)-13-Fluoroprostaglandin F_2α methyl ester was evaluated for pregnancy interruption in the hamster and smooth muscle stimulating properties on hamster uterine strips.