title: Total synthesis of sufentanil.
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 regioselective N-nucleophilic spiral epoxide cleavage with aniline promoted by Lewis acids.
authors.affiliation: College of Pharmacy, Seoul National University, Kwanak-Gu, Korea.
authors.forename: D Y
authors.initials: DY
authors.lastname: Shin
authors.forename: J S
authors.initials: JS
authors.lastname: Ryu
authors.forename: S S
authors.initials: SS
authors.lastname: Hyun
authors.forename: H J
authors.initials: HJ
authors.lastname: Park
authors.forename: R O
authors.initials: RO
authors.lastname: Jeon
authors.forename: Y G
authors.initials: YG
authors.lastname: Suh
mesh_terms: 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
chemical_list: D000701:Analgesics, Opioid; D007202:Indicators and Reagents; D008352:Mannich Bases; D017409:Sufentanil