Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl3/Sn or TiCl4/Sn bimetal redox system

H. Tanaka; M. Taniguchi; Y. Kameyama; M. Monnin; S. Torii; M. Sasaoka; T. Shiroi; S. Nagao; T. Yamada; Y. Tokumaru

doi:10.1246/bcsj.68.1385

Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl₃/Sn or TiCl₄/Sn bimetal redox system

H. Tanaka, M. Taniguchi, Y. Kameyama, M. Monnin, S. Torii, M. Sasaoka, T. Shiroi, S. Nagao, T. Yamada, Y. Tokumaru

Faculty of Engineering

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13 Citations (Scopus)

Abstract

A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)- 2-azetidinones by successive treatment with RuCl₃/HIO₄ and HIO₄/CuSO₄ and reductive cyclization of I-(I-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylth io)-2-azetidinones on treatment with a newly devised BiCl₃/Sn or TiCl₄/Sn bimetal redox couple in DMF containing pyridine.

Original language	English
Pages (from-to)	1385-1391
Number of pages	7
Journal	Bulletin of the Chemical Society of Japan
Volume	68
Issue number	5
DOIs	https://doi.org/10.1246/bcsj.68.1385
Publication status	Published - May 1995

ASJC Scopus subject areas

Chemistry(all)

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Tanaka, H., Taniguchi, M., Kameyama, Y., Monnin, M., Torii, S., Sasaoka, M., Shiroi, T., Nagao, S., Yamada, T., & Tokumaru, Y. (1995). Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl₃/Sn or TiCl₄/Sn bimetal redox system. Bulletin of the Chemical Society of Japan, 68(5), 1385-1391. https://doi.org/10.1246/bcsj.68.1385

Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl₃/Sn or TiCl₄/Sn bimetal redox system. / Tanaka, H.; Taniguchi, M.; Kameyama, Y. et al.
In: Bulletin of the Chemical Society of Japan, Vol. 68, No. 5, 05.1995, p. 1385-1391.

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

Tanaka, H, Taniguchi, M, Kameyama, Y, Monnin, M, Torii, S, Sasaoka, M, Shiroi, T, Nagao, S, Yamada, T & Tokumaru, Y 1995, 'Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl₃/Sn or TiCl₄/Sn bimetal redox system', Bulletin of the Chemical Society of Japan, vol. 68, no. 5, pp. 1385-1391. https://doi.org/10.1246/bcsj.68.1385

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abstract = "A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)- 2-azetidinones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reductive cyclization of I-(I-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylth io)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.",

author = "H. Tanaka and M. Taniguchi and Y. Kameyama and M. Monnin and S. Torii and M. Sasaoka and T. Shiroi and S. Nagao and T. Yamada and Y. Tokumaru",

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AU - Tanaka, H.

AU - Taniguchi, M.

AU - Kameyama, Y.

AU - Monnin, M.

AU - Torii, S.

AU - Sasaoka, M.

AU - Shiroi, T.

AU - Nagao, S.

AU - Yamada, T.

AU - Tokumaru, Y.

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AB - A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)- 2-azetidinones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reductive cyclization of I-(I-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylth io)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.

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Synthesis of 3-hydroxycephems from penicillin G through cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones promoted by a BiCl₃/Sn or TiCl₄/Sn bimetal redox system

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