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

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 borohydrid...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2024-11, Vol.9 (43), p.n/a
Main Authors: Adarsh, Doddegowdana Ramegowda, Teja, Thadakamalla Ravi, Vinaykumar, Allam, Sridhar, B., Reddy, B. V. Subba
Format: Article
Language:English
Subjects:
Acetonide protection
Amine‐anhydride coupling
Appel reaction
Diastereoselective reduction
Grignard reaction
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Summary: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. A highly diastereoselective synthesis of Eliglustat has been accomplised from D‐serine. The synthesis of a key precursor, syn‐1,2‐aminoalcohol has been achieved by the substrate directed reduction of carbonyl group. The overall process consists of nine steps with an overall yield of 21%.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202404952