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(c) Gould, S. J.; Melville, C. R.; Cone, M. C.; Chen, J.; Carney, J. R. J. Org. Chem. 1997, 62, 320.
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4
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4244188461
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Eur. Pat. Appl. EP 304,400 (CI C07D221/18), 22 Feb 1989, CH Appl. 87/3, 196, 20 Aug 1987
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For natural products related to the proposed intermediates in the biosynthesis, see: (a) Phenanthroviridin: Fendrich, G.; Zimmermann, W.; Gruner, J.; Auden, J. A. L. Eur. Pat. Appl. EP 304,400 (CI C07D221/18), 22 Feb 1989, CH Appl. 87/3, 196, 20 Aug 1987; Chem. Abstr. 1990, 112, 75295q.
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Fendrich, G.1
Zimmermann, W.2
Gruner, J.3
Auden, J.A.L.4
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5
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0001296631
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(b) Phenanthroviridone: Cone, M. C.; Melville, C. R.; Gore, M. P.; Gould, S. J. J. Org. Chem. 1993, 58, 1058.
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Cone, M.C.1
Melville, C.R.2
Gore, M.P.3
Gould, S.J.4
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6
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0026001391
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(c) Jadomycin A: Ayer, S. W.; McInnes, A. G.; Thibault, P.; Walter, J. A.; Doull, J. L.; Parnell, T.; Vining, L. C. Tetrahedron Lett. 1991, 32, 6301.
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Jadomycin, A.1
Ayer, S.W.2
McInnes, A.G.3
Thibault, P.4
Walter, J.A.5
Doull, J.L.6
Parnell, T.7
Vining, L.C.8
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7
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0027174569
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(d) Jadomycin B: Doull, J. L.; Ayer, S. W.; Singh, A. K.; Thibault, P. J. Antibiot. 1993, 46, 869.
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Jadomycin, B.1
Doull, J.L.2
Ayer, S.W.3
Singh, A.K.4
Thibault, P.5
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10
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84987335907
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Furusaki, A.; Matsui, M.; Watanabe, T.; Omura, S.; Nakagawa, A.; Hata, T. Isr. J. Chem. 1972, 10, 173.
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Furusaki, A.1
Matsui, M.2
Watanabe, T.3
Omura, S.4
Nakagawa, A.5
Hata, T.6
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11
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0027328956
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Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34, 4713.
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Echavarren, A.M.1
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Paredes, M.C.3
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0027997344
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(a) Mithani, S.; Weeratunga, G.; Taylor, N. J.; Dmitrienko, G. I. J. Am. Chem. Soc. 1994, 116, 2209.
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Mithani, S.1
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13
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0025291219
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(b) Dmitrienko, G. I.; Nielsen, K. E.; Steingart, C.; Ming, N. S.; Willson, J. M.; Weeratunga, G. Tetrahedron Lett. 1990, 31, 3681.
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Dmitrienko, G.I.1
Nielsen, K.E.2
Steingart, C.3
Ming, N.S.4
Willson, J.M.5
Weeratunga, G.6
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14
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0025158460
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(c) Weeratunga, G.; Prasad, G. K. B.; Dilley, J.; Taylor, N. J.; Dmitrienko, G. I. Tetrahedron Lett. 1990, 31, 5713.
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Weeratunga, G.1
Prasad, G.K.B.2
Dilley, J.3
Taylor, N.J.4
Dmitrienko, G.I.5
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15
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0028050438
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Gould, S. J.; Tamayo, N.; Melville, C. R.; Cone, M. C. J. Am. Chem. Soc. 1994, 116, 2207.
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Gould, S.J.1
Tamayo, N.2
Melville, C.R.3
Cone, M.C.4
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16
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0030980065
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For naturally occurring benzo[b]fluorenes, see: (a) Carney, J. R.; Hong, A.-T.; Gould, S. J. Tetrahedron Lett. 1997, 38, 3139.
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Tetrahedron Lett.
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Carney, J.R.1
Hong, A.-T.2
Gould, S.J.3
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18
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0027382038
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(c) Aoyama, T.; Zhao, W.; Kojima, F.; Muraoka, Y.; Naganawa, H.; Takeuchi, T.; Aoyagi, T. J. Antibiot. 1993, 46, 1471.
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Aoyama, T.1
Zhao, W.2
Kojima, F.3
Muraoka, Y.4
Naganawa, H.5
Takeuchi, T.6
Aoyagi, T.7
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19
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0026488221
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(d) Shin-ya, K.; Furihata, K.; Teshima, Y.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1992, 33, 7025.
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(1992)
Tetrahedron Lett.
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, pp. 7025
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Shin-Ya, K.1
Furihata, K.2
Teshima, Y.3
Hayakawa, Y.4
Seto, H.5
-
20
-
-
85036679087
-
-
See also reference 2b
-
(e) See also reference 2b.
-
-
-
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21
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0029801405
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Gould, S. J.; Chen, J.; Cone, M. C.; Gore, M. P., Melville, C. R.; Tamayo, N. J. Org. Chem. 1996, 61, 5720.
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Gould, S.J.1
Chen, J.2
Cone, M.C.3
Gore, M.P.4
Melville, C.R.5
Tamayo, N.6
-
23
-
-
85036682036
-
-
8b
-
8b
-
-
-
-
24
-
-
0006179060
-
-
For the related palladium-catalyzed coupling of quinone triflates, see: Echavarren, A. M.; Frutos, Ó.; Tamayo, N.; Noheda, P.; Calle, P. J. Org. Chem. 1997, 62, 4524.
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Echavarren, A.M.1
Frutos, Ó.2
Tamayo, N.3
Noheda, P.4
Calle, P.5
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25
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0026316055
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(a) Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56, 6488.
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Tamayo, N.1
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Paredes, M.C.3
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26
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0028135070
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(b) Tamayo, N.; Echavarren, A. M.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 6075.
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Tamayo, N.1
Echavarren, A.M.2
Cárdenas, D.J.3
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28
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0026502274
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For other synthetic work directed towards the synthesis of 1, see: (a) O'Sullivan, P. J.; Moreno, R.; Murphy, W. S. Tetrahedron Lett. 1992, 33, 535.
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Tetrahedron Lett.
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O'Sullivan, P.J.1
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Murphy, W.S.3
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(b) Estévez, J. C.; Estévez, R. J. Castedo, L. Tetrahedron Lett. 1993, 34, 6479.
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Estévez, J.C.1
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31
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0030817915
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(d) Williams, W.; Sun, X.; Jebaratnam, D. J. Org. Chem. 1997, 62, 4364.
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Williams, W.1
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34
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0023117386
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(b) Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19.
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Rawal, V.H.1
Jones, R.J.2
Cava, M.P.3
-
35
-
-
85036680919
-
-
Although formation of 17 could be explained by attack of the amino group or the carbamate at C-2 of the quinone, followed by migration of the aryl to C-3, no rearrangement was observed after treatment of 13 under basic conditions
-
Although formation of 17 could be explained by attack of the amino group or the carbamate at C-2 of the quinone, followed by migration of the aryl to C-3, no rearrangement was observed after treatment of 13 under basic conditions.
-
-
-
-
36
-
-
85036678778
-
-
19b
-
19b
-
-
-
-
37
-
-
0026681171
-
-
(b) For precedents on the isomerization of o-to p-quinones, see: Bekaert, A.; Andrieux, J.; Plat, M. Tetrahedron Lett. 1992, 33, 2805. Thomson, R. H. Naturally Occurring Quinones, Academic: London, 1971, pp. 206-209.
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Bekaert, A.1
Andrieux, J.2
Plat, M.3
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38
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0026681171
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Academic: London
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(b) For precedents on the isomerization of o-to p-quinones, see: Bekaert, A.; Andrieux, J.; Plat, M. Tetrahedron Lett. 1992, 33, 2805. Thomson, R. H. Naturally Occurring Quinones, Academic: London, 1971, pp. 206-209.
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Naturally Occurring Quinones
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Thomson, R.H.1
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40
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-
0013230836
-
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For the synthesis of the desmethyl derivative of 3 1: Liebeskind, L. S.; Iyer, S.; Jewell, C. F. J. Org. Chem. 1986, 51, 3067.
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J. Org. Chem.
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Liebeskind, L.S.1
Iyer, S.2
Jewell, C.F.3
-
41
-
-
85036678292
-
-
3N with BrCN is slower than N-cyanation for these substrates
-
3N with BrCN is slower than N-cyanation for these substrates.
-
-
-
-
42
-
-
0025785660
-
-
For lead references, see: (a) McIntire, W. S.; Wemmer, D. E.; Chistoserdov, A.; Lidstrom, M. E. Science 1991, 252, 817.
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McIntire, W.S.1
Wemmer, D.E.2
Chistoserdov, A.3
Lidstrom, M.E.4
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43
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0030453603
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(b) Bishop, G. R.; Valente, E. J., Whitehead, T. L.; Brown, K. L.; Hicks, R. P.; Davidson, V. L. J. Am. Chem. Soc. 1996, 118, 12868.
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Bishop, G.R.1
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Whitehead, T.L.3
Brown, K.L.4
Hicks, R.P.5
Davidson, V.L.6
-
44
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0001611378
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(c) Itoh, S.; Tanaka, N.; Haranou, S., Ando, T.; Komatsu, M.; Ohshiro, Y.; Fukuzumi, S. J. Org. Chem. 1996, 61, 8967.
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Itoh, S.1
Tanaka, N.2
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Komatsu, M.5
Ohshiro, Y.6
Fukuzumi, S.7
-
45
-
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0001259655
-
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and references therein
-
Itoh, S.; Mure, M.; Ogino, M.; Ohshiro, Y. J. Org. Chem. 1991, 56, 6857, and references therein.
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-
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Itoh, S.1
Mure, M.2
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Ohshiro, Y.4
-
46
-
-
33751499763
-
-
(a) Grunwell, J. R.; Karipides, A.; Wigal, C. T.; Heinzman, S. W.; Parlow, J.; Surso, J. A.; Clayton, L.; Fleitz, F. J.; Daffner, M.; Stevens, J. E. J. Org. Chem. 1991, 56, 91.
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-
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Grunwell, J.R.1
Karipides, A.2
Wigal, C.T.3
Heinzman, S.W.4
Parlow, J.5
Surso, J.A.6
Clayton, L.7
Fleitz, F.J.8
Daffner, M.9
Stevens, J.E.10
-
49
-
-
85036683721
-
-
13C correlations
-
13C correlations.
-
-
-
-
50
-
-
85036682447
-
-
The assignment was further supported by a NOESY experiment
-
The assignment was further supported by a NOESY experiment.
-
-
-
-
51
-
-
85036676721
-
-
3 in DMF (100 °C)
-
3 in DMF (100 °C).
-
-
-
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