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.
Authors
- D.R. Adarsh
- B. V. Subba Reddy (ORCID: https://orcid.org/0000-0003-0814-583X)
- Allam Vinaykumar
- Balasubramanian Sridhar (ORCID: https://orcid.org/0000-0002-9682-8376)
- T. Ravi Teja
Institutions
- Indian Institute of Chemical Technology (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- ChemistrySelect
- Published
- 2024-11-01
- DOI
- https://doi.org/10.1002/slct.202404952
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India