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Volumn 53, Issue 2, 1997, Pages 539-556

General and efficient synthesis of 2-alkylcarbapenems: Synthesis of dethiacarba analogs of clinically useful carbapenems via palladium-catalyzed cross-coupling reaction

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM DERIVATIVE;

EID: 0031012803     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00980-5     Document Type: Article
Times cited : (41)

References (26)
  • 7
    • 0025797165 scopus 로고
    • There have been several reports on the 2-(heteroatom-substituted methyl)carbapenems. For example, see: Imuta, M.; Itani, H.; Ona, H.; Konoike, T.; Uyeo, S.; Kimura, Y.; Miwa, H.; Matsuura, S.; Yoshida, T. Chem. Pharm. Bull. 1991, 39, 672. In this case, the adjacent heteroatom or the functional group activates the carbapenem skeleton and these carbapenems are beyond the scope of this paper.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 672
    • Imuta, M.1    Itani, H.2    Ona, H.3    Konoike, T.4    Uyeo, S.5    Kimura, Y.6    Miwa, H.7    Matsuura, S.8    Yoshida, T.9
  • 8
    • 0021717415 scopus 로고
    • 2-Alkylcarbapenem synthesis from carbapenam-2-one (a derivative of 7) has been reported by Wittig reaction with a stabilized phosphorus ylide. However, the product was a mixture including undesired carbapenam having an exocyclic double bond: de Vries, J. G.; Hauser, G.; Sigmund, G. Tetrahedron Lett., 1984, 25, 5989.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5989
    • De Vries, J.G.1    Hauser, G.2    Sigmund, G.3
  • 9
    • 0022550582 scopus 로고
    • For example, see: Fujimoto, K.; Iwano, Y.; Hirai, K. Bull. Chem. Soc. Jpn. 1986, 59, 1363. Recently, a new synthesis of 2-alkylcarbapenem was reported: Feigelson, G. B. Tetrahedron Lett., 1995, 36, 7407.
    • (1986) Bull. Chem. Soc. Jpn. , vol.59 , pp. 1363
    • Fujimoto, K.1    Iwano, Y.2    Hirai, K.3
  • 10
    • 0029133349 scopus 로고
    • For example, see: Fujimoto, K.; Iwano, Y.; Hirai, K. Bull. Chem. Soc. Jpn. 1986, 59, 1363. Recently, a new synthesis of 2-alkylcarbapenem was reported: Feigelson, G. B. Tetrahedron Lett., 1995, 36, 7407.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7407
    • Feigelson, G.B.1
  • 12
    • 0025299407 scopus 로고
    • Syntheses of 2-arylcarbapenems via the Stille cross-coupling reaction and the Suzuki cross-coupling reaction of carbapenem-2-yl triflates have been reported: (a) Rano, T. A.; Greenlee, M. L.; DiNinno, F. P. Tetrahedron Lett. 1990, 31, 2853.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2853
    • Rano, T.A.1    Greenlee, M.L.2    DiNinno, F.P.3
  • 22
    • 0027461573 scopus 로고
    • For recent examples of β-keto ester or amide alkylation with inversion of configuration, see: (a) Hoffman, R. V.; Kim, H.-O. Tetrahedron Lett. 1993, 34, 2051.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2051
    • Hoffman, R.V.1    Kim, H.-O.2
  • 26
    • 0342600929 scopus 로고    scopus 로고
    • note
    • The trial of NOESY experiment of 22 was unsuccessful due to overlapping of the pyrrolidine protons with those of the carbapenem skeleton.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.