Within the realm of medicinal chemistry, synthesis plays a pivotal role in any drug research and development endeavor. The ability to design elegant and economical synthetic routes is often a major factor for making a drug a commercial winner. Retrosynthetic analysis/ Synthon disconnection approach, introduced and advanced by Prof. E. J. Corey of Harvard University has served as a powerful driving force on design elegant and economical synthetic routes to any useful molecule of scientific or industrial interest. Exploiting the advantages of this approach, we have proposed a good number of synthesis schemes for a potent anti-diabetic drug ‘Pioglitazone’.from the results of its retrosynthetic analysis. The proposed synthesis planning being a theoretical explorations, the actual laboratory execution requires a cross examination of so many factors such as reactions, reagents and order of events. The routes that utilize readily available starting materials, convergent, economical, safe and produce maximum yield in short reaction time are most feasible.