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1
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0018640473
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(a) Imipenem: Leanza, W. J.; Wildonger, K. J.; Miller, T. W.; Christensen, B. G. J. Med. Chem. 1979, 22, 1435.
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J. Med. Chem.
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Leanza, W.J.1
Wildonger, K.J.2
Miller, T.W.3
Christensen, B.G.4
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2
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0020594264
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(b) Panipenem: Miyadera, T.; Sugimura, Y.; Hashimoto, T.; Tanaka, T.; Iino, K.; Shibata, T.; Sugawara, S. J. Antibiot. 1983, 36, 1034.
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J. Antibiot.
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Miyadera, T.1
Sugimura, Y.2
Hashimoto, T.3
Tanaka, T.4
Iino, K.5
Shibata, T.6
Sugawara, S.7
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3
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0026701599
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(c) Biapenem: Nagao, Y.; Nagase, Y.; Kumagai, T.; Matsunaga, H.; Abe, T.; Shimada, O.; Hayashi, T.; Inoue, Y. J. Org. Chem. 1992, 57, 4243.
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J. Org. Chem.
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Nagao, Y.1
Nagase, Y.2
Kumagai, T.3
Matsunaga, H.4
Abe, T.5
Shimada, O.6
Hayashi, T.7
Inoue, Y.8
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4
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0025279314
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(d) Meropenem: Sunagawa, M.; Matsumura, H.; Inoue, T.; Fukasawa, M.; Kato, M. J. Antibiot. 1990, 43, 519.
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J. Antibiot.
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Sunagawa, M.1
Matsumura, H.2
Inoue, T.3
Fukasawa, M.4
Kato, M.5
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5
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0029971256
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(e) S-4661: Iso, Y.; Irie, T.; Nishino, Y.; Motokawa, K.; Nishitani, Y. J. Antibiot. 1996, 49, 199.
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J. Antibiot.
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Iso, Y.1
Irie, T.2
Nishino, Y.3
Motokawa, K.4
Nishitani, Y.5
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7
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0025797165
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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.
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(1991)
Chem. Pharm. Bull.
, vol.39
, pp. 672
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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
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8
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0021717415
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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.
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Tetrahedron Lett.
, vol.25
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De Vries, J.G.1
Hauser, G.2
Sigmund, G.3
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9
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0022550582
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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.
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(1986)
Bull. Chem. Soc. Jpn.
, vol.59
, pp. 1363
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Fujimoto, K.1
Iwano, Y.2
Hirai, K.3
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10
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0029133349
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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.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 7407
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Feigelson, G.B.1
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12
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0025299407
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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.
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(1990)
Tetrahedron Lett.
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, pp. 2853
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Rano, T.A.1
Greenlee, M.L.2
DiNinno, F.P.3
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13
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0027229274
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(b) Yasuda, N.; Xavier, L.; Rieger, D. L.; Li, Y.; DeCamp, A. E.; Dolling, U.-H. Tetrahedron Lett. 1993, 34, 3211.
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(1993)
Tetrahedron Lett.
, vol.34
, pp. 3211
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Yasuda, N.1
Xavier, L.2
Rieger, D.L.3
Li, Y.4
DeCamp, A.E.5
Dolling, U.-H.6
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15
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0029928211
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Preliminary communication of this paper: Narukawa, Y.; Nishi, K.; Onoue, H. Tetrahedron Lett., 1996, 37, 2589.
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 2589
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Narukawa, Y.1
Nishi, K.2
Onoue, H.3
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16
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0021745572
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(a) Ueda, Y.; Roberge, G.; Vinet, V. Can. J. Chem. 1984, 62, 2936.
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(1984)
Can. J. Chem.
, vol.62
, pp. 2936
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Ueda, Y.1
Roberge, G.2
Vinet, V.3
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18
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0002662579
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(c) Shih, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Heterocycles, 1984, 21, 29.
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(1984)
Heterocycles
, vol.21
, pp. 29
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Shih, D.H.1
Baker, F.2
Cama, L.3
Christensen, B.G.4
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21
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0000545025
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Ohtani, M.; Watanabe, F.; Narisada, M. J. Org. Chem. 1984, 49, 5271.
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J. Org. Chem.
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, pp. 5271
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Ohtani, M.1
Watanabe, F.2
Narisada, M.3
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22
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0027461573
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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.
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(1993)
Tetrahedron Lett.
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Hoffman, R.V.1
Kim, H.-O.2
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23
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0024552973
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(b) McWhorter, W.; Fredenhagen, A.; Nakanishi, K.; Komura, H. Chem. Commun. 1989, 299.
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(1989)
Chem. Commun.
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McWhorter, W.1
Fredenhagen, A.2
Nakanishi, K.3
Komura, H.4
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25
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0001947228
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Prieto, J. A.; Suarez, J.; Larson, G. L. Synth. Commun. 1988, 18, 253
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(1988)
Synth. Commun.
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Prieto, J.A.1
Suarez, J.2
Larson, G.L.3
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26
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0342600929
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note
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The trial of NOESY experiment of 22 was unsuccessful due to overlapping of the pyrrolidine protons with those of the carbapenem skeleton.
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