Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems

Manabu Kuroboshi, Masayoshi Miyada, Syoichi Tateyama, Hideo Tanaka

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

(3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.

Original languageEnglish
Pages (from-to)1471-1484
Number of pages14
JournalHeterocycles
Volume76
Issue number2
DOIs
Publication statusPublished - Nov 1 2008

Fingerprint

Carbapenems
Chlorination
Halogenation
Desulfurization
Acylation
Oxides
Hot Temperature
Derivatives
2-azetidinone

Keywords

  • 4-Chloro-2-azetidinone
  • Carbapenem
  • Electrooxidative Chlorination
  • Electrooxidative Desulfurization/Chlorination
  • Rring Opening

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems. / Kuroboshi, Manabu; Miyada, Masayoshi; Tateyama, Syoichi; Tanaka, Hideo.

In: Heterocycles, Vol. 76, No. 2, 01.11.2008, p. 1471-1484.

Research output: Contribution to journalArticle

@article{4b61d6ca96534f38a31225cf72db93ec,
title = "Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems",
abstract = "(3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.",
keywords = "4-Chloro-2-azetidinone, Carbapenem, Electrooxidative Chlorination, Electrooxidative Desulfurization/Chlorination, Rring Opening",
author = "Manabu Kuroboshi and Masayoshi Miyada and Syoichi Tateyama and Hideo Tanaka",
year = "2008",
month = "11",
day = "1",
doi = "10.3987/COM-08-S(N)110",
language = "English",
volume = "76",
pages = "1471--1484",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "2",

}

TY - JOUR

T1 - Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems

AU - Kuroboshi, Manabu

AU - Miyada, Masayoshi

AU - Tateyama, Syoichi

AU - Tanaka, Hideo

PY - 2008/11/1

Y1 - 2008/11/1

N2 - (3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.

AB - (3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.

KW - 4-Chloro-2-azetidinone

KW - Carbapenem

KW - Electrooxidative Chlorination

KW - Electrooxidative Desulfurization/Chlorination

KW - Rring Opening

UR - http://www.scopus.com/inward/record.url?scp=61349192654&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=61349192654&partnerID=8YFLogxK

U2 - 10.3987/COM-08-S(N)110

DO - 10.3987/COM-08-S(N)110

M3 - Article

AN - SCOPUS:61349192654

VL - 76

SP - 1471

EP - 1484

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 2

ER -