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

Department of Pharmaceutical Sciences

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

2 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

Bibliographical note

Funding Information:
This work was supported by the Korea Science and Engineering Foundation (KOSEF) through the Research Center for New Drug Development and partly by Research Institute of Pharmaceutical Science at Seoul National University.

Keywords

Analgesics
Oxirane
Piperidine
Sufentanil
Total Synthesis

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10.1007/BF02979064

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@article{0313a56aadd2448ebb059a03ca05b030,

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}",

note = "Funding Information: This work was supported by the Korea Science and Engineering Foundation (KOSEF) through the Research Center for New Drug Development and partly by Research Institute of Pharmaceutical Science at Seoul National University.",

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

N1 - Funding Information: This work was supported by the Korea Science and Engineering Foundation (KOSEF) through the Research Center for New Drug Development and partly by Research Institute of Pharmaceutical Science at Seoul National University.

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 - http://www.scopus.com/inward/record.url?scp=0033174964&partnerID=8YFLogxK

U2 - 10.1007/BF02979064

DO - 10.1007/BF02979064

M3 - Article

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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

Bibliographical note

Keywords

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