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Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
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Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
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Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
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Weymeth-Wilson, A.C.1
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Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
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Murphy, J.A.1
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5
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0002125235
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Reviews on synthesis: H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 41; H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 93.
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Lhermitte, H.1
Grierson, D.S.2
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6
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0002125234
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Reviews on synthesis: H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 41; H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 93.
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Lhermitte, H.1
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0027521713
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K. C. Nicolaou, C. W. Hummel, M. Nakada, K. Shibayama, E. N. Pitsinos, H. Saimoto, Y. Mizuno, K.-U. Baldenius and A. L. Smith, J. Am. Chem. Soc., 1993, 115, 7625; S. A. Hitchcock, M. Y. Chu-Moyer, S. H. Boyer, S. H. Olson and S. J. Danishefsky, J. Am. Chem. Soc., 1995, 117, 5750.
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Nicolaou, K.C.1
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8
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0029004091
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K. C. Nicolaou, C. W. Hummel, M. Nakada, K. Shibayama, E. N. Pitsinos, H. Saimoto, Y. Mizuno, K.-U. Baldenius and A. L. Smith, J. Am. Chem. Soc., 1993, 115, 7625; S. A. Hitchcock, M. Y. Chu-Moyer, S. H. Boyer, S. H. Olson and S. J. Danishefsky, J. Am. Chem. Soc., 1995, 117, 5750.
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Hitchcock, S.A.1
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D. L. J. Clive, Y. Bo, Y.; Y. Tao, S. Daigneault, Y.-J. Wu and G. Meignan, J. Am. Chem. Soc., 1998, 120, 10 332.
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D. L. J. Clive, Y. Bo, N. Selvakumar, R. McDonald and B. D. Santarsiero, Tetrahedron, 1999, 55, 3277.
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12
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0025741330
-
-
Synthesis of racemic calicheamicinone: (a) J. N. Haseltine, M. Paz Cabal, N. B. Mantlo, N. Iwasawa, D. S. Yamashita, R. S. Coleman, S. J. Danishefsky and G. K. Schulte, J. Am. Chem. Soc., 1991, 113, 3850;
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Haseltine, J.N.1
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Coleman, R.S.6
Danishefsky, S.J.7
Schulte, G.K.8
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(b) I. Churcher, D. Hallet and P. D. Magnus, J. Am. Chem. Soc., 1998, 120, 10350.
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Churcher, I.1
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-
14
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-
0027370770
-
-
Synthesis of optically pure calicheamicinone: A. L. Smith, E. N. Pitsinos, C.-K. Hwang, Y. Mizuno, H. Saimoto, G. R. Scarlato, T. Suzuki and K. C. Nicolaou, J. Am. Chem. Soc., 1993, 115, 7612; J. Aiyer, S. A. Hitchcock, D. Denhart, K. K. C. Liu, S. J. Danishefsky and D. M. Crothers, Angew. Chem., Int. Ed. Engl, 1994, 33, 855.
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Smith, A.L.1
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Saimoto, H.5
Scarlato, G.R.6
Suzuki, T.7
Nicolaou, K.C.8
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15
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0027952280
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-
Synthesis of optically pure calicheamicinone: A. L. Smith, E. N. Pitsinos, C.-K. Hwang, Y. Mizuno, H. Saimoto, G. R. Scarlato, T. Suzuki and K. C. Nicolaou, J. Am. Chem. Soc., 1993, 115, 7612; J. Aiyer, S. A. Hitchcock, D. Denhart, K. K. C. Liu, S. J. Danishefsky and D. M. Crothers, Angew. Chem., Int. Ed. Engl, 1994, 33, 855.
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Aiyer, J.1
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16
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37049086057
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and references therein
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P. Magnus, R. T. Lewis and F. Bennett, J. Chem. Soc., Chem. Commun., 1989, 916 and references therein.
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0000593953
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Cf. S. Danishefsky, M. P. Prisbylla and S. Hiner, J. Am. Chem. Soc., 1978, 100, 2918; S. Danishefsky, Acc. Chem. Res., 1981, 14, 400.
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Danishefsky, S.1
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Cf. S. Danishefsky, M. P. Prisbylla and S. Hiner, J. Am. Chem. Soc., 1978, 100, 2918; S. Danishefsky, Acc. Chem. Res., 1981, 14, 400.
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Danishefsky, S.1
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0343895171
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Cf. K. Utimoto, A. Nakamura and S. Matsubara, J. Am. Chem. Soc., 1990, 112, 8189.
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H. Kunz and C. Unverzagt, Angew. Chem., Int. Ed. Engl., 1984, 23, 436.
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H. Hofmeister, K. Annen, H. Laurent and R. Wiechert, Angew. Chem., Int. Ed. Engl., 1984, 23, 727.
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Hofmeister, H.1
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J. K. Whitesell, A. Bhattacharya, C. M. Buchanan, H. H. Chen, D. Deyo, D. James, C.-L. Liu and M. A. Minton, Tetrahedron, 1986, 42, 2993.
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Whitesell, J.K.1
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0027495578
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R. D. Groneberg, T. Miyazaki, N. A. Stylianides, T. J. Schulze, W. Stahl, E. P. Schreiner, T. Suzuki, Y. Iwabuchi, A. L. Smith and K. C. Nicolaou, J. Am. Chem. Soc., 1993, 115, 7593.
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Groneberg, R.D.1
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Suzuki, T.7
Iwabuchi, Y.8
Smith, A.L.9
Nicolaou, K.C.10
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33
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0001291489
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Cf. G. A. Molander, J. B. Etter, L. S. Harring and P.-J. Thorel, J. Am. Chem. Soc., 1991, 113, 8036.
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34
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0343459540
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note
-
O-Methylation, DIBAL-H reduction of the ester to an aldehyde and acid-catalyzed desilylation and ring closure gave a pyranose with cis nitrogen and OMe groups, indicating that the hydroxy stereochemistry in 83 (major isomer) required inversion.
-
-
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35
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0343459538
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(a) For synthesis of a model from D-glucose, see: F. L. Van Delft, G. A. Van Der Marel and J. H. Van Boom, Carbohydrate Lett., 1996, 2, 53;
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Van Delft, F.L.1
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0025141467
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(c) D. Kahne, D. Yang and M. D. Lee, Tetrahedron Lett., 1990, 31, 21;
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Kahne, D.1
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38
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0343023829
-
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ref. 21
-
(d) ref. 21;
-
-
-
-
39
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45149133385
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(e) for synthesis from methyl 2-deoxy-β-D-ribofuranoside, see: E. A. Mash, S. K. Nimkar and S. M. DeMoss, J. Carbohydr. Chem., 1995, 14, 1369.
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Mash, E.A.1
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Demoss, S.M.3
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0029038220
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(f) R. H. Halcomb, S. H. Boyer, M. D. Wittman, S. H. Olson, D. J. Denhart, K. K. C. Liu and S. J. Danishefsky, J. Am. Chem. Soc., 1995, 117, 5720;
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Halcomb, R.H.1
Boyer, S.H.2
Wittman, M.D.3
Olson, S.H.4
Denhart, D.J.5
Liu, K.K.C.6
Danishefsky, S.J.7
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0029932272
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(g) P. Crotti, V. Di Bussolo, L. Favero, F. Macchia and M. Pineschi, Tetrahedron: Asymmetry, 1996, 7, 779;
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Crotti, P.1
Bussolo, V.D.2
Favero, L.3
Macchia, F.4
Pineschi, M.5
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42
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0030852346
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(h) F. Badalassi, P. Crotti, L. Favero, F. Macchia and M. Pineschi, Tetrahedron, 1997, 53, 14369.
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Badalassi, F.1
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Macchia, F.4
Pineschi, M.5
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43
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37049078784
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M. Hirama, I. Nishizaki, T. Shigemoto and S. Itô, J. Chem. Soc., Chem. Commun., 1986, 393.
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Hirama, M.1
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Itô, S.4
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46
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0024445971
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(b) for synthesis from 2,6-dideoxy-α-D-ribohexopyranose, see: K. Van Laak and H.-D. Scharf, Tetrahedron Lett., 1989, 30, 4505;
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-
-
Van Laak, K.1
Scharf, H.-D.2
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47
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0028309516
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(c) for synthesis based on Sharpless kinetic resolution, see: W. R. Roush and D. Gustin, Tetrahedron Lett., 1994, 35, 4931;
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Tetrahedron Lett.
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-
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Roush, W.R.1
Gustin, D.2
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48
-
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0027940051
-
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(d) for synthesis from D-fucose, see: S.-H. Kim, D. Augen, D. Yang and D. Kahne, J. Am. Chem. Soc., 1994, 116, 1766;
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Kim, S.-H.1
Augen, D.2
Yang, D.3
Kahne, D.4
-
49
-
-
0002429536
-
-
see ref 21
-
(e) for synthesis from 4,6-O-benzylidene-D-allal (R. U. Lemieux, E. Fraga and K. A. Watanabe, Can. J. Chem. 1968, 46, 61), see ref 21.
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Can. J. Chem.
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Lemieux, R.U.1
Fraga, E.2
Watanabe, K.A.3
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50
-
-
84986665025
-
-
ref. 21
-
For synthesis of a model from D-galactose, see: H. Rainer and H.-D. Scharf, Liebigs Ann. Chem., 1993, 117; ref. 21; for synthesis from crotonaldehyde, see: W. R. Roush and B. C. Follows, Tetrahedron Lett., 1994, 35, 4935; for synthesis from di-O-actyl-d-fucal, see ref. 24(f).
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Liebigs Ann. Chem.
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Rainer, H.1
Scharf, H.-D.2
-
51
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0028365023
-
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for synthesis from di-O-actyl-d-fucal, see ref. 24(f)
-
For synthesis of a model from D-galactose, see: H. Rainer and H.-D. Scharf, Liebigs Ann. Chem., 1993, 117; ref. 21; for synthesis from crotonaldehyde, see: W. R. Roush and B. C. Follows, Tetrahedron Lett., 1994, 35, 4935; for synthesis from di-O-actyl-d-fucal, see ref. 24(f).
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Roush, W.R.1
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0029879373
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A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 2521.
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55
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0342589577
-
-
note
-
The route from 114 is similar to that reported by Danishefsky and coworkers [see ref. 24(f).
-
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56
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0024220049
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J. Mariño-Albernas, V. Verez-Bencomo, L. Gonzalez-Rodriguez, C. S. Perez-Martinez, E. Gonzalez-Abreu Castell and A. Gonzalez-Segredo, Carbohydr. Res., 1988, 183, 175.
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Gonzalez-Segredo, A.6
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57
-
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0343023822
-
-
note
-
For synthesis from D-rhamnose, see ref. 21(d); ref. 21; for synthesis from di-O-acetyl-L-rhamnal, see ref. 24(f).
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59
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0004955374
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