Total synthesis of sufentanil

Dong Yun Shin; Jae Sang Ryu; Soon Sil Hyun; Hyun Ju Park; Ra Ok Jeon; Young Ger Suh

doi:10.1007/BF02979064

Total synthesis of sufentanil

Dong Yun Shin
, Jae Sang Ryu
, Soon Sil Hyun
, Hyun Ju Park
, Ra Ok Jeon
, Young Ger Suh

Seoul National University

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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.

Original language	English
Pages (from-to)	398-400
Number of pages	3
Journal	Archives of Pharmacal Research
Volume	22
Issue number	4
DOIs	https://doi.org/10.1007/BF02979064
State	Published - Aug 1999
Externally published	Yes

Keywords

Analgesics
Oxirane
Piperidine
Sufentanil
Total Synthesis

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10.1007/BF02979064

Cite this

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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.",

keywords = "Analgesics, Oxirane, Piperidine, Sufentanil, Total Synthesis",

author = "Shin, \{Dong Yun\} and Ryu, \{Jae Sang\} and Hyun, \{Soon Sil\} and Park, \{Hyun Ju\} and Jeon, \{Ra Ok\} and Suh, \{Young Ger\}",

year = "1999",

month = aug,

doi = "10.1007/BF02979064",

language = "English",

volume = "22",

pages = "398--400",

journal = "Archives of Pharmacal Research",

issn = "0253-6269",

publisher = "Pharmaceutical Society of Korea",

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TY - JOUR

T1 - Total synthesis of sufentanil

AU - Shin, Dong Yun

AU - Ryu, Jae Sang

AU - Hyun, Soon Sil

AU - Park, Hyun Ju

AU - Jeon, Ra Ok

AU - Suh, Young Ger

PY - 1999/8

Y1 - 1999/8

N2 - 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.

AB - 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.

KW - Analgesics

KW - Oxirane

KW - Piperidine

KW - Sufentanil

KW - Total Synthesis

UR - https://www.scopus.com/pages/publications/0033174964

U2 - 10.1007/BF02979064

DO - 10.1007/BF02979064

M3 - Article

C2 - 10489880

AN - SCOPUS:0033174964

SN - 0253-6269

VL - 22

SP - 398

EP - 400

JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

IS - 4

ER -

Total synthesis of sufentanil

Abstract

Keywords

Access to Document

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