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Article

Total Synthesis of Eliglustat via Diastereoselective Amination of Chiral para-Methoxycinnamyl Benzyl Ether

by
Younggyu Kong
,
Pulla Reddy Boggu
,
Gi Min Park
,
Yeon Su Kim
,
Seong Hwan An
,
In Su Kim
and
Young Hoon Jung
*
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(8), 2603; https://doi.org/10.3390/molecules27082603
Submission received: 22 March 2022 / Revised: 7 April 2022 / Accepted: 14 April 2022 / Published: 18 April 2022
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

Eliglustat (Cerdelga®, Genzyme Corp. Cambridge, MA, USA) is an approved drug for a non-neurological type of Gaucher disease. Herein, we describe the total synthesis of eliglustat 1 starting from readily available 1,4-benzodioxan-6-carbaldehyde via Sharpless asymmetric dihydroxylation and diastereoselective amination of chiral para-methoxycinnamyl benzyl ethers using chlorosulfonyl isocyanate as the key steps. Notably, the reaction between syn-1,2-dibenzyl ether 6 and chlorosulfonyl isocyanate in the mixture of toluene and hexane (10:1) afforded syn-1,2-amino alcohol 5 at a 62% yield with a diastereoselectivity > 20:1. This observation can be explained by competition between the SNi and the SN1 mechanisms, leading to the retention of stereochemistry.
Keywords: amination; eliglustat; chlorosulfonyl isocyanate; Sharpless asymmetric dihydroxylation; total synthesis amination; eliglustat; chlorosulfonyl isocyanate; Sharpless asymmetric dihydroxylation; total synthesis

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MDPI and ACS Style

Kong, Y.; Boggu, P.R.; Park, G.M.; Kim, Y.S.; An, S.H.; Kim, I.S.; Jung, Y.H. Total Synthesis of Eliglustat via Diastereoselective Amination of Chiral para-Methoxycinnamyl Benzyl Ether. Molecules 2022, 27, 2603. https://doi.org/10.3390/molecules27082603

AMA Style

Kong Y, Boggu PR, Park GM, Kim YS, An SH, Kim IS, Jung YH. Total Synthesis of Eliglustat via Diastereoselective Amination of Chiral para-Methoxycinnamyl Benzyl Ether. Molecules. 2022; 27(8):2603. https://doi.org/10.3390/molecules27082603

Chicago/Turabian Style

Kong, Younggyu, Pulla Reddy Boggu, Gi Min Park, Yeon Su Kim, Seong Hwan An, In Su Kim, and Young Hoon Jung. 2022. "Total Synthesis of Eliglustat via Diastereoselective Amination of Chiral para-Methoxycinnamyl Benzyl Ether" Molecules 27, no. 8: 2603. https://doi.org/10.3390/molecules27082603

APA Style

Kong, Y., Boggu, P. R., Park, G. M., Kim, Y. S., An, S. H., Kim, I. S., & Jung, Y. H. (2022). Total Synthesis of Eliglustat via Diastereoselective Amination of Chiral para-Methoxycinnamyl Benzyl Ether. Molecules, 27(8), 2603. https://doi.org/10.3390/molecules27082603

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