A Facile Route for Synthesis of (±)-Dinoprost, (±)-Carboprost and Its Analogs

Abstract

Prostaglandins are a family of 20-carbon fatty acids found in virtually all mammalian cells 1,2. These are highly biologically active and have been implicated in the mediation of many physiological responses 3,4. Natural prostaglandins possess an allylic, secondary alcohol group at C-15 position. This alcohol group can be oxidized into a ketone in the presence of 15hydroxyprostaglandin dehydrogenase and this process is very rapid in vivo in animals and man 5-7. The oxidation to 15-ketoprostaglandins leads to the inactivation of prostaglandin

A Novel Synthesis of 5E-Isomer-Free Carboprost Methyl Ester

“…7a,7b This method had more selectivity than the one reported by Shakar et. al 8 in the Grignard addition step, and gave compound 7 with 70% desired 15S-isomer and only 30% unwanted 15R-isomer. However, approximate 3% 5(E)-isomer was also found in the upper side chain (α chain) in the Wittig reaction step.…”

“…7 This method had more selectivity than the one reported by Shankar et. al 8 in the Grignard addition step and gave compound 7 with 70% desired 15S-isomer and only 30% unwanted 15R-isomer. However, ca.…”