Synthesis plays a central role in any pharmaceutica l development endeavor. Design synthetic routes to pharmaceuticals/drugs in convergent and efficient m anner are very fundamental to synthetic organic/med icinal chemistry. Synthon disconnection approach / retrosy nthetic analysis advocated by Prof.E.J.Corey has em erged as powerful means in designing synthetic routes to sma ll molecule pharmaceuticals. Taking the privilege o f this approach, a number of synthesis schemes has been pr oposed for a potent anti-hypertensive drug ‘Captopr il’ on the basis of its retrosynthetic analysis. The proposed synthesis schemes being a theoretical exploration, the actual laboratory implementation requires the cross examin ation of a considerable number of factors such as r eactions, reagents and order of events. Generally, the route which is cost-effective, safe, employ readily avail able starting materials and produce maximum yield in a short reac tion time under robust condition is most viable .