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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)7445-7448
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number50
DOIs
Publication statusPublished - Dec 9 1991

Fingerprint

Lactams
Penicillin G
Anti-Bacterial Agents
2-azetidinone

Keywords

  • exo-methylene penam
  • intramolecular Michael addition
  • β-lactam antibiotics

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis. / Tanaka, Hideo; Kameyama, Yutaka; Kosaka, Atsuko; Yamauchi, Takahito; Torii, Sigeru.

In: Tetrahedron Letters, Vol. 32, No. 50, 09.12.1991, p. 7445-7448.

Research output: Contribution to journalArticle

Tanaka, Hideo ; Kameyama, Yutaka ; Kosaka, Atsuko ; Yamauchi, Takahito ; Torii, Sigeru. / A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesis. In: Tetrahedron Letters. 1991 ; Vol. 32, No. 50. pp. 7445-7448.
@article{1af383d20b314e618525dcb46ad3c71e,
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",
year = "1991",
month = "12",
day = "9",
doi = "10.1016/0040-4039(91)80130-X",
language = "English",
volume = "32",
pages = "7445--7448",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "50",

}

TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=0026333001&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026333001&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(91)80130-X

DO - 10.1016/0040-4039(91)80130-X

M3 - Article

VL - 32

SP - 7445

EP - 7448

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

ER -