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34
-
-
33644941034
-
-
note
-
Compound 7 is available in six steps (37% overall) from methyl gallate using three recrystallizations and was scaled to 300 g, ref 6.
-
-
-
-
35
-
-
33644956309
-
-
note
-
Compound 6 is available in five steps (55% overall) from (R)-4-hydroxyphenyl-glycine using two recrystallizations and was scaled to 60 g, ref 7a.
-
-
-
-
36
-
-
33644965777
-
-
note
-
Benzyl ether deprotection at higher temperatures (25 °C) may lead to competitive aryl bromide reduction, although this was observed in appreciable amounts only when excess Raney nickel was employed.
-
-
-
-
37
-
-
33644939186
-
-
note
-
Saponification of 11 was considerably slower than that of 10 and occasionally required additional LiOH for complete conversion to 12, with little effect on the amount of epimer generated in the reaction.
-
-
-
-
38
-
-
33644932759
-
-
note
-
Compound 13 is available in three steps (45% overall) from 4-fluoro-3-nitrobenzaldehyde and was scaled to 30 g, ref 6.
-
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-
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39
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0029918444
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41
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33644938211
-
-
note
-
Recent efforts have led to improvements in the vancomycin CD ring closure, and this method was utilized for the preparation of the analogous intermediates bearing a residue 4/5 thioamide. Its use in the preparation of 5 along with additional vancomycin analogues will be disclosed in due time.
-
-
-
-
42
-
-
33644941900
-
-
note
-
Use of Raney nickel for N-Cbz removal was also successful, although lower recoveries (84%) of the product were observed.
-
-
-
-
43
-
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33644954972
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-
note
-
2.
-
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44
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Ramanjulu, J.M.7
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0032538485
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(b) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. 1998, 37, 2708.
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46
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(c) Nicolaou, K. C.; Jain, N. F.; Natarajan, S.; Hughes, R.; Solomon, M. E.; Li, H.; Ramanjulu, J. M.; Takayanagi, M.; Koumbis, A. E.; Bando, T. Angew. Chem., Int. Ed. 1998, 37, 2714.
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33644958368
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note
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Reduction of the nitro group was sensitive to the choice of solvent in terms of recovery and observance of side products.
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