Total synthesis of sufentanil.
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 regioselective N-nucleophilic spiral epoxide cleavage with aniline promoted by Lewis acids.
Shin
D Y
DY
College of Pharmacy, Seoul National University, Kwanak-Gu, Korea.
Ryu
J S
JS
Hyun
S S
SS
Park
H J
HJ
Jeon
R O
RO
Suh
Y G
YG
D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008352:Mannich Bases; D013055:Spectrophotometry, Infrared; D017409:Sufentanil / Q000138:chemical synthesis* / Q000737:chemistry
D000701:Analgesics, Opioid; D007202:Indicators and Reagents; D008352:Mannich Bases; D017409:Sufentanil