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Volumn 66, Issue 3, 2013, Pages 161-163

A practical preparation of the key intermediate for penems and carbapenems synthesis

Author keywords

b lactams; Kinugasa reaction; penems and cabapenems synthesis

Indexed keywords

ACETYLENE; AMMONIA; AURANOFIN; AZETIDINONE DERIVATIVE; BETA LACTAM ANTIBIOTIC; CARBAPENEM; COPPER; GLYOXYLIC ACID DERIVATIVE; HYDROXYLAMINE; LITHIUM; NITRONE DERIVATIVE; PENEM DERIVATIVE; SODIUM;

EID: 84875709185     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2013.8     Document Type: Article
Times cited : (9)

References (21)
  • 4
    • 0030028910 scopus 로고    scopus 로고
    • Preparations of two pivotal intermediates for the synthesis of 1-b-methyl carbapenem antibiotics
    • Berks, A. H. Preparations of two pivotal intermediates for the synthesis of 1-b-methyl carbapenem antibiotics. Tetrahedron 52, 331-375 (1996).
    • (1996) Tetrahedron , vol.52 , pp. 331-375
    • Berks, A.H.1
  • 6
    • 85010174894 scopus 로고
    • 2-(Alkylthio)penem-3-carboxylic acids. IV. Synthesis of (hydroxyethyl)-azetidinone precursors to 1-thia analogs of thienamycin
    • Yoshida, A., Hayashi, T., Takeda, N., Oida, S. & Ohki, E. 2-(Alkylthio)penem-3-carboxylic acids. IV. Synthesis of (hydroxyethyl)- azetidinone precursors to 1-thia analogs of thienamycin. Chem. Pharm. Bull. 29, 2899-2909 (1981).
    • (1981) Chem. Pharm. Bull , vol.29 , pp. 2899-2909
    • Yoshida, A.1    Hayashi, T.2    Takeda, N.3    Oida, S.4    Ohki, E.5
  • 7
    • 0022970513 scopus 로고
    • Novel Synthesis of (3R4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy) ethyl]-2-azetidinone the Versatile Key Intermediate of Carbapenem Syn thesis, from (S)-ethyl lactate
    • Ito, Y., Kawabata, T. & Terashima, S. A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate. Tetrahedron Lett. 27, 5751-5754 (1986).
    • (1986) Tetrahedron Lett , vol.27 , pp. 5751-5754
    • Ito, Y.1    Kawabata, T.2    Terashima, S.A.3
  • 8
    • 0026770958 scopus 로고
    • Synthetic studies of carbapenem and penem antibiotics. II. Synthesis of 3-acetyl-2-azetidinones by [22] cycloaddition of diketene and Schiff bases
    • Sasaki, A., Goda, K., Enomoto, M. & Sunagawa, M. Synthetic studies of carbapenem and penem antibiotics. II. Synthesis of 3-acetyl-2-azetidinones by [22]-cycloaddition of diketene and Schiff bases. Chem. Pharm. Bull. 40, 1094-1097 (1992).
    • (1992) Chem. Pharm. Bull , vol.40 , pp. 1094-1097
    • Sasaki, A.1    Goda, K.2    Enomoto, M.3    Sunagawa, M.4
  • 9
    • 84887263006 scopus 로고    scopus 로고
    • Synthesis of 3-acetyl-2-azetidinones by [22] cycloaddition of diketene and imines
    • Yang, M. G., Jung, H. L., Jin, S. C. & Young, Y. L. Synthesis of 3-acetyl-2-azetidinones by [22] cycloaddition of diketene and imines. Bull. Korean Chem. Soc. 17, 985-987 (1996).
    • (1996) Bull. Korean Chem. Soc , vol.17 , pp. 985-987
    • Yang, M.G.1    Jung, H.L.2    Jin, S.C.3    Young, Y.L.4
  • 13
    • 0033766956 scopus 로고    scopus 로고
    • Novel synthesis of ()-4-Acetoxy-3-hydroxyethyl-2-azetidinone from carbohydrate. A formal total synthesis of ()-thienamycin
    • Tatsuta, K., Takahashi, M., Tanaka, N. & Chikauchi, K. Novel synthesis of ()-4-Acetoxy-3-hydroxyethyl-2-azetidinone from carbohydrate. A formal total synthesis of ()-thienamycin. J. Antibiot. 53, 1231-1234 (2000).
    • (2000) J. Antibiot , vol.53 , pp. 1231-1234
    • Tatsuta, K.1    Takahashi, M.2    Tanaka, N.3    Chikauchi, K.4
  • 14
    • 80051753721 scopus 로고    scopus 로고
    • A formal synthesis of ezetimibe via Kinugasa cycloaddition/ rearrangement cascade
    • Michalak, M. et al. A formal synthesis of ezetimibe via Kinugasa cycloaddition/ rearrangement cascade. J. Org. Chem. 76, 6931-6936 (2011).
    • (2011) J. Org. Chem , vol.76 , pp. 6931-6936
    • Michalak, M.1
  • 15
    • 78449252251 scopus 로고    scopus 로고
    • Direct, catalytic synthesis of carbapenams via cycloaddition/ rearrangement cascade reaction: Unexpected acetylenes' structure effect
    • Mames, A. et al. Direct, catalytic synthesis of carbapenams via cycloaddition/ rearrangement cascade reaction: unexpected acetylenes' structure effect. J. Org. Chem. 75, 7580-7587 (2010).
    • (2010) J. Org. Chem , vol.75 , pp. 7580-7587
    • Mames, A.1
  • 16
    • 65249149260 scopus 로고    scopus 로고
    • Asymmetric Kinugasa reaction of cyclic nitrones and non-racemic acetylenes
    • Stecko, S., Mames, A., Furman, B. & Chmielewski, M. Asymmetric Kinugasa reaction of cyclic nitrones and non-racemic acetylenes. J. Org. Chem. 74, 3094-3100 (2009).
    • (2009) J. Org. Chem , vol.74 , pp. 3094-3100
    • Stecko, S.1    Mames, A.2    Furman, B.3    Chmielewski, M.4
  • 17
    • 52449102186 scopus 로고    scopus 로고
    • Diastereoselective synthesis of carbapenams via Kinugasa reaction
    • Stecko, S., Mames, A., Furman, B. & Chmielewski, M. Diastereoselective synthesis of carbapenams via Kinugasa reaction. J. Org. Chem. 73, 7402-7404 (2008).
    • (2008) J. Org. Chem , vol.73 , pp. 7402-7404
    • Stecko, S.1    Mames, A.2    Furman, B.3    Chmielewski, M.4
  • 18
    • 84869494293 scopus 로고    scopus 로고
    • Synthesis of N,4-diaryl substituted b-lactams via Kinugasa cycloaddition/rearrangement reaction
    • Michalak, M. et al. Synthesis of N,4-diaryl substituted b-lactams via Kinugasa cycloaddition/rearrangement reaction. Tetrahedron 68, 10806-10817 (2012).
    • (2012) Tetrahedron , vol.68 , pp. 10806-10817
    • Michalak, M.1
  • 19
    • 84866008137 scopus 로고    scopus 로고
    • An entry to carbapenem antibiotics scaffold via asymmetric Kinugasa reaction
    • Maciejko, M. et al. An entry to carbapenem antibiotics scaffold via asymmetric Kinugasa reaction. Synthesis 2825-2839 (2012).
    • (2012) Synthesis , pp. 2825-2839
    • MacIejko, M.1
  • 21
    • 84856729522 scopus 로고    scopus 로고
    • Practical synthetic approach to 4-acetoxy-2-azetidinone for the preparation of carbapenem and penem antibiotics
    • Zhou, G. B., Guan, Y. Q., Tang, H., Zhao, Y. B. & Yang, L. R. Practical synthetic approach to 4-acetoxy-2-azetidinone for the preparation of carbapenem and penem antibiotics. Res. Chem. Intermed. 38, 251-259 (2012).
    • (2012) Res. Chem. Intermed , vol.38 , pp. 251-259
    • Zhou, G.B.1    Guan, Y.Q.2    Tang, H.3    Zhao, Y.B.4    Yang, L.R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.