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

Manabu Kuroboshi; Masayoshi Miyada; Syoichi Tateyama; Hideo Tanaka

doi:10.3987/COM-08-S(N)110

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 journal › Article

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 language	English
Pages (from-to)	1471-1484
Number of pages	14
Journal	Heterocycles
Volume	76
Issue number	2
DOIs	https://doi.org/10.3987/COM-08-S(N)110
Publication status	Published - 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

Kuroboshi, M., Miyada, M., Tateyama, S., & Tanaka, H. (2008). Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems. Heterocycles, 76(2), 1471-1484. https://doi.org/10.3987/COM-08-S(N)110

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 journal › Article

Kuroboshi, M, Miyada, M, Tateyama, S & Tanaka, H 2008, 'Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems', Heterocycles, vol. 76, no. 2, pp. 1471-1484. https://doi.org/10.3987/COM-08-S(N)110

Kuroboshi M, Miyada M, Tateyama S, Tanaka H. Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems. Heterocycles. 2008 Nov 1;76(2):1471-1484. https://doi.org/10.3987/COM-08-S(N)110

Kuroboshi, Manabu ; Miyada, Masayoshi ; Tateyama, Syoichi ; Tanaka, Hideo. / Electrooxidative desulfurization/chlorination. A facile synthesis of 4-chloro-2-azetidinones, a potent intermediate for carbapenems. In: Heterocycles. 2008 ; Vol. 76, No. 2. pp. 1471-1484.

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10.3987/COM-08-S(N)110