Issue 72, 2019, Issue in Progress

Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (−)-shikimic acid

Abstract

N-Octyl-β-valienamine (NOV) 1 and N-octyl-4-epi-β-valienamine (NOEV) 2 are potent chemical chaperone drug candidates for the therapy of lysosomal storage disorders. Novel stereoselective syntheses of NOV 1 and NOEV 2 starting from naturally abundant (−)-shikimic acid are described in this article. The common key intermediate compound 5 was first synthesized from readily available (−)-shikimic acid via 9 steps in 50% yield. Compound 5 was then converted to NOV 1 via 5 steps in 61% yield, and it was also converted to NOEV 2 via 8 steps in 38% yield. In summary, NOV 1 was synthesized via 14 steps in 31% overall yield; and NOEV 2 was synthesized via 17 steps in 19% overall yield.

Graphical abstract: Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (−)-shikimic acid

Supplementary files

Article information

Article type
Paper
Submitted
07 Nov 2019
Accepted
04 Dec 2019
First published
18 Dec 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 42077-42084

Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (−)-shikimic acid

F. Li, J. Yu, W. Ding, M. Sun, Y. He, X. Zhu, S. Liu and X. Shi, RSC Adv., 2019, 9, 42077 DOI: 10.1039/C9RA09235H

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