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Theander, O.1
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31
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0039115214
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See ref. 5, p. 170. 3-Bromocatechol
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From 2-chloro-6-methylphenol: (i) See ref. 5, p. 170. 3-Bromocatechol.
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32
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0001541118
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From 2,3-dimethoxybromobenzene: (j) H. S. Mason, J. Am. Chem. Soc., 1947, 69, 2241.
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Mason, H.S.1
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34
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0040893279
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3 to 3-bromocatechol (8). 3-Chlorocatechol
-
3 to 3-bromocatechol (8). 3-Chlorocatechol.
-
-
-
-
35
-
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0039707320
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-
Commercially available from TCI America, at $376/g
-
(m) Commercially available from TCI America, at $376/g.
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-
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37
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0025811349
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From 3-chlorophenol: (o) F. Chiocarra, P. D. Gennaro, G. L. Monica, R. Sebastino and B. Rindone, Tetrahedron, 1991, 47, 4429.
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0010285624
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3-Iodocatechol
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From 1-chloro-2,3-dimethoxybenzene: (p) E. Hornbaker and A. Burger, J. Am. Chem. Soc., 1955, 77, 5314. 3-Iodocatechol.
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Hornbaker, E.1
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39
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0014352369
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3-Methoxycatechol
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(q) To our knowledge, 3-iodocatechol has not been prepared by chemical means. Enzymatic preparation: D. T. Gibson, J. R. Koch, C. L. Schmid and R. E. Kallio, Biochemistry, 1968, 7, 3795. 3-Methoxycatechol.
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Gibson, D.T.1
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Kallio, R.E.4
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40
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0029008505
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From 3-methoxybenzene-1,2-diol: (r) J. A. Guzman, V. Mendoza, E. Garcia, C. F. Garibay, L. Z. Olivares and L. A. Maldonado, Synth. Commun., 1995, 25, 2121;
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Guzman, J.A.1
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41
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0007235741
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and references cited therein
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From 2,6-dimethoxyphenol: (s) J. Morey, A. Costa, D. M. Pere, G. Suner and J. M. Saa, J. Org. Chem., 1990, 55, 3902 and references cited therein.
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0009538175
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From 1,2,3-trihydroxybenzene: (t) B. I. Kamara, E. V. Brandt and D. Ferreira, Tetrahedron, 1999, 55, 861;
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Kamara, B.I.1
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45
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0039707309
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3-Methoxy-6-methylcatechol
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From 4-methyl-1,2,3-trimethoxybenzene: (w) C. Carvalho and M. V. Sargyn, J. Chem. Soc., Chem. Commun., 1984, 227. 3-Methoxy-6-methylcatechol.
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Carvalho, C.1
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From 2,3,4-trimethoxytoluene: (y) C. F. Carvalho and M. V. Sargent, J. Chem. Soc., Chem. Commun., 1984, 4, 227;
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Boberg, M.1
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49
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0014352369
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of making catechols through enzymatic means
-
To the best of our knowledge, there exist only three methods (in addition to the original report by Gibson: D. T. Gibson, J. R. Koch, C. L. Schmid and R. E. Kallio, Biochemistry, 1968, 7, 3795) of making catechols through enzymatic means.
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Biochemistry
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Gibson, D.T.1
Koch, J.R.2
Schmid, C.L.3
Kallio, R.E.4
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50
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0000501863
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Frost's process involves the use of E. Coli AB2834/pKD136/pKD9.069A and conversion of glucose to catechol: (a) K. M. Draths, D. L. Pompliani, D. L. Conley, J. W. Frost, A. Berry, G. L. Disbrow, R. J. Staversky and J. C. Lievense, J. Am. Chem. Soc., 1992, 114, 3956;
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Draths, K.M.1
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Berry, A.5
Disbrow, G.L.6
Staversky, R.J.7
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52
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eds. P. T. Anastas and T. C. Williamson, Oxford University Press, New York, NY
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(c) K. M. Draths and J. W. Frost, in Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, eds. P. T. Anastas and T. C. Williamson, Oxford University Press, New York, NY, 1998, 150.
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Draths, K.M.1
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53
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Enzymatic oxidation of substituted 2-nitrophenols to various catechols with nitrophenol oxygenase has been reported: (d) B. R. Folsom, R. Stierli, R. P. Schwarzenbach and J. Zeyer, Environ. Sci. Technol., 1994, 28, 306.
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Folsom, B.R.1
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Recently, Yoshida and co-workers reported a new organism capable of oxidizing aromatic rings to catechol in one step: (e) Y. Yoshida, Y. Ikura and T. Kudo, Biosci. Biotechnol. Biochem., 1997, 61, 46.
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Biosci. Biotechnol. Biochem.
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Yoshida, Y.1
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55
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0030851951
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The synthesis of, for example, catechol (i) (Fig. 1), the precursor for narciclasine (2), is long and arduous: (a) T. J. Doyle, M. Hendrix, D. VanDerveer, S. Javanmard and J. Haseltine, Tetrahedron, 1997, 53, 11153.
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Tetrahedron
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Doyle, T.J.1
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Haseltine, J.5
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56
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0039115211
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manuscript in preparation; see also refs. 2 and 3 above
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Its direct preparation by biooxidation would greatly simplify current routes to the alkaloids: (b) T. Hudlicky, D. Gonzalez, S. Schilling, H. Akgün, T. Martinot, U. Rinner, C. Chan and G. R. Pettit, J. Org. Chem., 2001, manuscript in preparation; see also refs. 2 and 3 above.
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J. Org. Chem.
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Hudlicky, T.1
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T. Hudlicky, M. R. Stabile, D. T. Gibson and G. M. Whited, Org. Synth., 1999, 76, 77.
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(a) T. Hudlicky, M. A. Endoma and G. Butora, J. Chem. Soc., Perkin Trans. 1, 1996, 2187;
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Hudlicky, T.1
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(b) M. R. Stabile, T. Hudlicky, M. L. Meisels, G. Butora, A. G. Gum, S. P. Fearnley, A. J. Thorpe and M. R. Ellis, Chirality, 1995, 7, 556.
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Stabile, M.R.1
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Thorpe, A.J.7
Ellis, M.R.8
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