Substrate Directed Highly Diastereoselective Synthesis of Eliglustat: A Drug for Gaucher Disease

Abstract

A highly diastereoselective total synthesis of Eliglustat has been accomplished starting from a readily available D-serine. This novel route involves a four-step telescoped process to afford the keto intermediate (4) in 74% overall yield. The diastereoselective reduction of 4 using sodium borohydride provides the alcohol, a key intermediate 5, with excellent selectivity (>99 dr) and yield (95%). The total synthesis of Eliglustat from D-serine has been accomplished in ten steps with an overall yield of 21%. This process not only gives a desirable yield but also avoids the use of hazardous conditions.