Archives of Pharmacal Research

, 22:398

Total synthesis of sufentanil

  • Dong-Yun Shin
  • Jae-Sang Ryu
  • Soon-Sil Hyun
  • Hyun-Ju Park
  • Ra-Ok Jeon
  • Young-Ger Suh
Research Articles Medicinal Chemistry

DOI: 10.1007/BF02979064

Cite this article as:
Shin, DY., Ryu, JS., Hyun, SS. et al. Arch Pharm Res (1999) 22: 398. doi:10.1007/BF02979064
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Abstract

Sufentanil, a potent anilidopiperidine analgesic, was synthesized from a simple thiophenylethylamine via six step sequence. The key parts of this synthesis involved an efficient construction of thiophenylethylpiperidone by aminomethano desilylation-cyclization followed by Swern oxidation and a direct regioselectiveN-nucleophilic spiral epoxide cleavage with aniline promoted by Lewis acids.

Key words

Total SynthesisSufentanilAnalgesicsPiperidineOxirane

Copyright information

© The Pharmaceutical Society of Korea 1999

Authors and Affiliations

  • Dong-Yun Shin
    • 1
  • Jae-Sang Ryu
    • 1
  • Soon-Sil Hyun
    • 1
  • Hyun-Ju Park
    • 1
  • Ra-Ok Jeon
    • 1
  • Young-Ger Suh
    • 1
  1. 1.College of PharmacySeoul National UniversitySeoulKorea