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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 1via 5 steps in 61% yield, and it was also converted to NOEV 2via 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.

SUBMITTER: Li FL

PROVIDER: S-EPMC9076550 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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

Li Feng-Lei FL Yu Jiang-Ping JP Ding Wei W Sun Mian-Mian MM He Yun-Gang YG Zhu Xing-Liang XL Liu Shi-Ling SL Shi Xiao-Xin XX

RSC advances 20191218 72

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 1via< ...[more]

PMID: 35542836

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