A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis

Hideo Tanaka; Yutaka Kameyama; Atsuko Kosaka; Takahito Yamauchi; Sigeru Torii

doi:10.1016/0040-4039(91)80130-X

A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis

Hideo Tanaka, Yutaka Kameyama, Atsuko Kosaka, Takahito Yamauchi, Sigeru Torii

Faculty of Engineering

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

12 Citations (Scopus)

Abstract

A convenient synthesis of 2-exo-methylene penams 1 was performed by transformation of thiazoline-azetidinones, derived from penicillin G, through intramolecular Michael addition. Manipulation of the exo-methylene moiety of 1 opened new entries to 2-oxopenam and 2β-thiomethyl substituted penams, respectively.

Original language	English
Pages (from-to)	7445-7448
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	50
DOIs	https://doi.org/10.1016/0040-4039(91)80130-X
Publication status	Published - Dec 9 1991

Keywords

exo-methylene penam
intramolecular Michael addition
β-lactam antibiotics

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(91)80130-X

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title = "A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis",

abstract = "A convenient synthesis of 2-exo-methylene penams 1 was performed by transformation of thiazoline-azetidinones, derived from penicillin G, through intramolecular Michael addition. Manipulation of the exo-methylene moiety of 1 opened new entries to 2-oxopenam and 2β-thiomethyl substituted penams, respectively.",

keywords = "exo-methylene penam, intramolecular Michael addition, β-lactam antibiotics",

author = "Hideo Tanaka and Yutaka Kameyama and Atsuko Kosaka and Takahito Yamauchi and Sigeru Torii",

note = "Funding Information: This work was supported in part by a Grant-in Aid for Co-operative Research No. 03233102 from The Ministry of Education, Science, and Culture of Japan. The authors are grateful to the SC-NMR Laboratory of Okayama University for the measurement of 1H NMR spectra.",

year = "1991",

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doi = "10.1016/0040-4039(91)80130-X",

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T1 - A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis

AU - Tanaka, Hideo

AU - Kameyama, Yutaka

AU - Kosaka, Atsuko

AU - Yamauchi, Takahito

AU - Torii, Sigeru

N1 - Funding Information: This work was supported in part by a Grant-in Aid for Co-operative Research No. 03233102 from The Ministry of Education, Science, and Culture of Japan. The authors are grateful to the SC-NMR Laboratory of Okayama University for the measurement of 1H NMR spectra.

PY - 1991/12/9

Y1 - 1991/12/9

N2 - A convenient synthesis of 2-exo-methylene penams 1 was performed by transformation of thiazoline-azetidinones, derived from penicillin G, through intramolecular Michael addition. Manipulation of the exo-methylene moiety of 1 opened new entries to 2-oxopenam and 2β-thiomethyl substituted penams, respectively.

AB - A convenient synthesis of 2-exo-methylene penams 1 was performed by transformation of thiazoline-azetidinones, derived from penicillin G, through intramolecular Michael addition. Manipulation of the exo-methylene moiety of 1 opened new entries to 2-oxopenam and 2β-thiomethyl substituted penams, respectively.

KW - exo-methylene penam

KW - intramolecular Michael addition

KW - β-lactam antibiotics

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JF - Tetrahedron Letters

IS - 50

ER -

A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis

Abstract

Keywords

ASJC Scopus subject areas

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