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Charest, M. G.; Lerner, C. D.: Brubaker, J. D.; Siegel, D. R.; Myers, A. G. Science 2005, 308, 395.
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Science
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Charest, M.G.1
Lerner, C.D.2
Brubaker, J.D.3
Siegel, D.R.4
Myers, A.G.5
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6
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34548543627
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Myers, A. G.; Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R. Synthesis of Tetracyclines and Analogues Thereof. PCT/US05/ 17831, May 20. 2005.
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(a) Myers, A. G.; Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R. Synthesis of Tetracyclines and Analogues Thereof. PCT/US05/ 17831, May 20. 2005.
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7
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34548533568
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Myers, A. G. PCT/US07/66253, April 6, 2007.
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(b) Myers, A. G. PCT/US07/66253, April 6, 2007.
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8
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34548535450
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The Muxfeldt route to the tetracyclines (involving late-stage C- and D-ring constructions) was used to synthesize a number of analogs, and was scaled to provide (±)-6-thiatetracycline for early clinical trials (discontinued due to an apparent CNS-based toxicity), (a) Cunha, B. A. Clinical Uses of the Tetracyclines. In Handbook of Experimental Pharmacology; Hlavka, J. J., Boothe, J. H., Eds.; Springer-Verlag: New York, 1985; 78, p 393.
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The Muxfeldt route to the tetracyclines (involving late-stage C- and D-ring constructions) was used to synthesize a number of analogs, and was scaled to provide (±)-6-thiatetracycline for early clinical trials (discontinued due to an apparent CNS-based toxicity), (a) Cunha, B. A. Clinical Uses of the Tetracyclines. In Handbook of Experimental Pharmacology; Hlavka, J. J., Boothe, J. H., Eds.; Springer-Verlag: New York, 1985; Vol. 78, p 393.
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9
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0003709372
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Nelson, M, Hillen, W, Greenwald, R. A, Eds, Birkhäuser Verlag: Boston, MA
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(b) Tetracyclines in Biology, Chemistry, and Medicine; Nelson, M., Hillen, W., Greenwald, R. A., Eds.; Birkhäuser Verlag: Boston, MA, 2001; p 237.
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Tetracyclines in Biology, Chemistry, and Medicine
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10
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0001970379
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Riess, R.; Schön, M.; Laschat, S.; Jäger, V. Eur. J. Org. Chem. 1998, 473.
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Eur. J. Org. Chem
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Riess, R.1
Schön, M.2
Laschat, S.3
Jäger, V.4
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12
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0026050799
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Use of lithium N-methylephedrate for the enantioselective addition of 1-alkenylzinc bromides to aldehydes: Oppolzer, W.; Radinov, R. N. Tetrahedron Lett 1991, 32, 5777.
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(a) Use of lithium N-methylephedrate for the enantioselective addition of 1-alkenylzinc bromides to aldehydes: Oppolzer, W.; Radinov, R. N. Tetrahedron Lett 1991, 32, 5777.
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13
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34548537004
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Synthesis of dialkylzinc reagents by addition of Grignard, reagents to zinc chloride followed by precipitation with 1,4-dioxane: von dem Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719.
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(b) Synthesis of dialkylzinc reagents by addition of Grignard, reagents to zinc chloride followed by precipitation with 1,4-dioxane: von dem Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719.
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14
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0001064329
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Use of (1S,2R)-2-morpholin-4-yl-lphenylpropanol for the enantioselective addition of diisopropylzinc to aldehydes: Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
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(c) Use of (1S,2R)-2-morpholin-4-yl-lphenylpropanol for the enantioselective addition of diisopropylzinc to aldehydes: Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
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15
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15644370082
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Synthesis of (lS,2R)-2-pyrrolidiny-l-phenylpropanol by alkylation of norephedrine with 1,4-dibromobutane: Pierce, M. E. et al. J. Org. Chem. 1998, 63, 8536.
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(d) Synthesis of (lS,2R)-2-pyrrolidiny-l-phenylpropanol by alkylation of norephedrine with 1,4-dibromobutane: Pierce, M. E. et al. J. Org. Chem. 1998, 63, 8536.
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0037028571
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Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 2002.
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J. Am. Chem. Soc
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Layton, M.E.1
Morales, C.A.2
Shair, M.D.3
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17
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0002904790
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Furan 2-carboxaldehydes: (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19.
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Furan 2-carboxaldehydes: (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19.
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18
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0033230731
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(b) Sato, I.; Saito, T.; Omiya, D.; Takizawa, Y.; Soai, K. Heterocycles 1999, 57, 2753.
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Heterocycles
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Sato, I.1
Saito, T.2
Omiya, D.3
Takizawa, Y.4
Soai, K.5
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21
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33845280542
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Benson, S. C.; Cai, P.; Colon, M.; Haiza, M. A.; Tokles, M.; Snyder, J. K. J. Org. Chem. 1988, 53, 5335.
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J. Org. Chem
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Benson, S.C.1
Cai, P.2
Colon, M.3
Haiza, M.A.4
Tokles, M.5
Snyder, J.K.6
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22
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34548528452
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Prepared by Villsmeier-Haack formylation (Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1) of 3-methoxyfurfural, synthesized in hundredgram amounts-without chromatography-in four steps from 3-chloro-l,2propanediol:
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Prepared by Villsmeier-Haack formylation (Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1) of 3-methoxyfurfural, synthesized in hundredgram amounts-without chromatography-in four steps from 3-chloro-l,2propanediol:
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34548536740
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Allylic metalation (removal of the proton a to the dimethylamino group) is competitive with metalation of the isoxazole ring at higher temperatures and it is the predominant reaction pathway when bases other than n-butyllithium are used for deprotonation. A preliminary experiment with the 4-iodoisoxazole 9 (see Supporting Information) reveals that magnesium-halogen exchange at -20°C provides an efficient means of anion formation; trapping with 3-methoxyfurfural (6) gives a higher proportion of the (S)-alcohol 7. Magnesium-halogen exchange: (a) Wakefield, B. J. Preparation of Organomagnesium Compounds. In Organomagnesium Compounds in Organic Synthesis; Academic Press, Inc.: San Diego, 1995; pp 51-59.
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Allylic metalation (removal of the proton a to the dimethylamino group) is competitive with metalation of the isoxazole ring at higher temperatures and it is the predominant reaction pathway when bases other than n-butyllithium are used for deprotonation. A preliminary experiment with the 4-iodoisoxazole 9 (see Supporting Information) reveals that magnesium-halogen exchange at -20°C provides an efficient means of anion formation; trapping with 3-methoxyfurfural (6) gives a higher proportion of the (S)-alcohol 7. Magnesium-halogen exchange: (a) Wakefield, B. J. Preparation of Organomagnesium Compounds. In Organomagnesium Compounds in Organic Synthesis; Academic Press, Inc.: San Diego, 1995; pp 51-59.
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(b) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. Engl. 2000, 39, 4414.
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Angew. Chem., Int. Ed. Engl
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Boudier, A.1
Bromm, L.O.2
Lotz, M.3
Knochel, P.4
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26
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34548532881
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After 105 h at 95 °C cyclization of the (S)-alcohol 7 had proceeded to 89% conversion whereas cyclization of the (R)-alcohol 7 had proceeded to 77% conversion.
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After 105 h at 95 °C cyclization of the (S)-alcohol 7 had proceeded to 89% conversion whereas cyclization of the (R)-alcohol 7 had proceeded to 77% conversion.
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0030845835
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Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.
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(1997)
Tetrahedron
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Kappe, C.O.1
Murphree, S.S.2
Padwa, A.3
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33746215059
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Pieniazek, S. N.; Houk, K. N. Angew. Chem., Int. Ed. Engl. 2006, 45, 1442.
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(2006)
Angew. Chem., Int. Ed. Engl
, vol.45
, pp. 1442
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Pieniazek, S.N.1
Houk, K.N.2
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