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Nathans D. In: Gottlieb D., and Shaw P.D. (Eds). Antibiotics Vol. 1 (1967), Springer, New York 259-277
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Nathans, D.1
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Jiang M.X., Jin B., Gage J.L., Priour A., Savela G., and Miller M.J. J. Org. Chem. 71 (2006) 4164-4169
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Donohoe T.J., Bataille C.J.R., Gattrell W., Kloesges J., and Rossignol E. Org. Lett. 9 (2007) 1725-1728
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Rossignol, E.5
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24
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33845350198
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For the synthesis of 3a, see:
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For the synthesis of 3a, see:. McGuigan C., Hassan-Abdallah A., Srinivasan S., Wang Y., Siddiqui A., Daluge S.M., Gudmundsson K.S., Zhou H., McLean E.W., Peckham J.P., Burnette T.C., Marr H., Hazen R., Condreay L.D., Johnson L., and Balzarini J. J. Med. Chem. 49 (2006) 7215-7226
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McGuigan, C.1
Hassan-Abdallah, A.2
Srinivasan, S.3
Wang, Y.4
Siddiqui, A.5
Daluge, S.M.6
Gudmundsson, K.S.7
Zhou, H.8
McLean, E.W.9
Peckham, J.P.10
Burnette, T.C.11
Marr, H.12
Hazen, R.13
Condreay, L.D.14
Johnson, L.15
Balzarini, J.16
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28
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77953120866
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note
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4 in the presence of t-BuOCl and NaOH. The substrate was not compatible with the harsh oxidizing conditions and a complex product mixture resulted within 10 min; compound (±)-9a was not observed by this method.
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29
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0037032268
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For tethered aminohydroxylations with allyl carbamates as substrates, see:
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For tethered aminohydroxylations with allyl carbamates as substrates, see:. Donohoe T.J., Johnson P.D., Cowley A., and Keenan M. J. Am. Chem. Soc. 124 (2002) 12934-12935
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(2002)
J. Am. Chem. Soc.
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Donohoe, T.J.1
Johnson, P.D.2
Cowley, A.3
Keenan, M.4
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31
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4143087960
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For tethered amino-hydroxylations with homoallyl carbamates as substrates, see:
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For tethered amino-hydroxylations with homoallyl carbamates as substrates, see:. Kenworthy M.N., McAllister G.D., and Taylor R.J.K. Tetrahedron Lett. 45 (2004) 6661-6664
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(2004)
Tetrahedron Lett.
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Kenworthy, M.N.1
McAllister, G.D.2
Taylor, R.J.K.3
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34
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33644653551
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Donohoe T.J., Chughtai M.J., Klauber D.J., Griffin D., and Campbell A.D. J. Am. Chem. Soc. 128 (2006) 2514-2515
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J. Am. Chem. Soc.
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Donohoe, T.J.1
Chughtai, M.J.2
Klauber, D.J.3
Griffin, D.4
Campbell, A.D.5
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36
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77953123610
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note
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Attempts to directly prepare N-hydroxycarbamate (±)-7a from (±)-5a occurred with limited success. When homoallylic alcohol (±)-5a was stirred with CDI for 2 h and then treated with a solution of hydroxylamine hydrochloride and triethylamine, starting material (±)-5a was recovered and low conversion to N-hydroxycarbamate (±)-7a was observed.
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37
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33645410730
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For preparation of O-p-methoxybenzylhydroxylamine hydrochloride, see:
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For preparation of O-p-methoxybenzylhydroxylamine hydrochloride, see:. Zhu G., Yang F., Balachandran R., Hook P., Vallee R.B., Curran D.P., and Day B.W. J. Med. Chem. 49 (2006) 2063-2076
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J. Med. Chem.
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Zhu, G.1
Yang, F.2
Balachandran, R.3
Hook, P.4
Vallee, R.B.5
Curran, D.P.6
Day, B.W.7
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38
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84982367300
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a <7 for the NH of O-acylhydroxamic acids, see:
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a <7 for the NH of O-acylhydroxamic acids, see:. Bauer L., and Exner O. Angew. Chem., Int. Ed. Engl. 13 (1974) 376-385
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(1974)
Angew. Chem., Int. Ed. Engl.
, vol.13
, pp. 376-385
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Bauer, L.1
Exner, O.2
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39
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77953120777
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note
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LC-MS of the crude reaction mixture indicated that (±)-8a was the major component of the reaction mixture (74%). Unreacted (±)-7a (16%), N-mono-benzolylated product (3%), and bis-benzolylated product (7%) were also present.
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40
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0028589329
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Katagiri N., Ito Y., Kitano K., Toyota A., and Kaneko C. Chem. Pharm. Bull. 42 (1994) 2653-2655
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(1994)
Chem. Pharm. Bull.
, vol.42
, pp. 2653-2655
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Katagiri, N.1
Ito, Y.2
Kitano, K.3
Toyota, A.4
Kaneko, C.5
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41
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0001376012
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Diastereofacial addition will be directed anti to the electron rich bonds that stabilize the developing antibonding orbitals in the transition state, see:
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Diastereofacial addition will be directed anti to the electron rich bonds that stabilize the developing antibonding orbitals in the transition state, see:. Cieplak A.S. Chem. Rev. 99 (1999) 1265-1336
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(1999)
Chem. Rev.
, vol.99
, pp. 1265-1336
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Cieplak, A.S.1
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43
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77953121585
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note
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Carbamates have been observed as by-products in tethered aminohydroxylations, see: Ref. 13b, footnote 7.
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44
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77953122628
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note
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An imidotrioxoosmium (VII) species is proposed in the tethered aminohydroxylation reaction mechanism, see: Ref. 16b.
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46
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77953120495
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note
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Refer to Supplementary data for complete carbon and proton assignments for (±)-9a and (-)-9b.
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