Research Articles Medicinal Chemistry

Archives of Pharmacal Research

, Volume 22, Issue 4, pp 398-400

Total synthesis of sufentanil

  • Dong-Yun ShinAffiliated withCollege of Pharmacy, Seoul National University
  • , Jae-Sang RyuAffiliated withCollege of Pharmacy, Seoul National University
  • , Soon-Sil HyunAffiliated withCollege of Pharmacy, Seoul National University
  • , Hyun-Ju ParkAffiliated withCollege of Pharmacy, Seoul National University
  • , Ra-Ok JeonAffiliated withCollege of Pharmacy, Seoul National University
  • , Young-Ger SuhAffiliated withCollege of Pharmacy, Seoul National University Email author 

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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 Synthesis Sufentanil Analgesics Piperidine Oxirane