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0000390007
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Grindley, T. B.; Thangarasa, R. Can. J. Chem. 1990, 68, 1007. Although the regioselective benzyl protection of 2-hydroxyl of compound 9 was reported in ref 12a, under similar conditions, PMB-protection led to a roughly 1:1 mixture of the two possible isomers. The 2-hydroxyl group of compound 9 can also be selectively acetylated. However, the following benzylation led to a complex mixture due to the acetyl migration.
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Grindley, T.B.1
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0033516601
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Leeuwenburgh, M. A.; Kalker, C.; Duynstee, H. I.; Overkleeft, H. S.; van der Marcel, G. A.; van Boom, J. H. Tetrahedron 1999, 55, 8253.
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23
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45449124035
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2 hydrochloride and the subsequent protection of the amino group with a Boc group, the nitrile could not be reduced to the corresponding aldehyde under various conditions.
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Czernecki, S.1
Valery, J.-M.2
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24
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0030915529
-
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2 hydrochloride and the subsequent protection of the amino group with a Boc group, the nitrile could not be reduced to the corresponding aldehyde under various conditions.
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Arndt, H.1
Polborn, K.2
Koert, U.3
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25
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33947553765
-
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2 hydrochloride and the subsequent protection of the amino group with a Boc group, the nitrile could not be reduced to the corresponding aldehyde under various conditions.
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J. Am. Chem. Soc.
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Brown, H.C.1
Garg, C.P.2
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26
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0003110776
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(a) Hashimoto, H.; Asano, K.; Fujii, F.; Yoshimura, J. Carbohydr. Res. 1982, 104, 87. (b) Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283. The aziridine was prepared in less than 10% yield from the cyanohydrin of aldehyde 15 due to the reductive cleavage of the mesylate by LAH. The Lewis acid-mediated aziridine opening by benzyl alcohol also failed.
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0028876602
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(a) Hashimoto, H.; Asano, K.; Fujii, F.; Yoshimura, J. Carbohydr. Res. 1982, 104, 87. (b) Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283. The aziridine was prepared in less than 10% yield from the cyanohydrin of aldehyde 15 due to the reductive cleavage of the mesylate by LAH. The Lewis acid-mediated aziridine opening by benzyl alcohol also failed.
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Effenberger, F.1
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Van Delft, F.1
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Matsumoto, T.1
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32
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0000404274
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MacManus, D. A.; Grabowska, U.; Biggadike, K.; Bird, M. I.; Davies, S.; Vulfson, E. N.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1999, 295.
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0000894454
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(a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
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Cha, J.K.1
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33748610978
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(b) Christ, W. J.; Cha, J. K.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947.
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41
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(c) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.
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Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 19, 1977.
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43
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0000363937
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44
-
-
0346318572
-
-
note
-
13C NMR of compound 23 indicated that the newly formed resonance was at 94.48 ppm with a coupling constant of 170.35 Hz.
-
-
-
-
45
-
-
0346948540
-
-
Ph.D. Thesis, University of Notre Dame
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McKee, J. A. Ph.D. Thesis, University of Notre Dame, 1991.
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McKee, J.A.1
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0035835041
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Kim, H.; Kim, I. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 35.
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48
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0034686602
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Bessodes, M.; Dubertret, C.; Jasin, G.; Scherman, D. Bioorg. Med. Chem. Lett. 2000, 10, 1393. Alternatively, the E-oxime was prepared as a protected carbonyl compound (Barili, P. L.; Berti. G.; D'Andrea, F.; Di Bussolo, V. Carbohydr. Res. 1996, 290, 17). This also provided an easy entry to salmycin A. Unfortunately, although the silyl ether deprotection and acylation could be conducted without incident to afford the desired acid, the final coupling reaction with compound 28 failed to afford the desired product.
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Bessodes, M.1
Dubertret, C.2
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49
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0030603081
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Bessodes, M.; Dubertret, C.; Jasin, G.; Scherman, D. Bioorg. Med. Chem. Lett. 2000, 10, 1393. Alternatively, the E-oxime was prepared as a protected carbonyl compound (Barili, P. L.; Berti. G.; D'Andrea, F.; Di Bussolo, V. Carbohydr. Res. 1996, 290, 17). This also provided an easy entry to salmycin A. Unfortunately, although the silyl ether deprotection and acylation could be conducted without incident to afford the desired acid, the final coupling reaction with compound 28 failed to afford the desired product.
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-
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Barili, P.L.1
Berti, G.2
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-
50
-
-
0348209161
-
-
note
-
The siderophore conjugate was prepared with the 2′-hydroxyl group protected with an acetyl group. However. deacetylation caused the simultaneous cleavage of the ester linkage.
-
-
-
-
51
-
-
0346318571
-
-
note
-
Although the coupling reaction of acid 31 and compound 28 afforded the desired conjugate, this compound was too sensitive to survive the DDQ-mediated PMB deprotection.
-
-
-
|