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0039863113
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note
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Dedicated to the memory of Joseph E. Semple.
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0039271426
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Abstracts of papers
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San Francisco, CA, March 26-30, American Chemical Society: Washington, DC, 2000; ORGN.667
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Semple, J. E. Abstracts of Papers, 219th National Meeting of the American Chemical Society, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC, 2000; ORGN.667.
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(2000)
219th National Meeting of the American Chemical Society
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Semple, J.E.1
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3
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0032493411
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Taxol: (a) Ha, H. J.; Park, G. S.; Ahn, Y. G.; Lee, G. S. Bioorg. Med. Chem. Lett. 1998, 8, 1619.
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Ha, H.J.1
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(b) Review: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem., Intl. Ed. Engl. 1994, 106, 38.
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Nicolaou, K.C.1
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Semple, J. E.; Rowley, D. C.; Brunck, T. K. Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 7, 315.
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Bioorg. Med. Chem. Lett.
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Semple, J.E.1
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Brunck, T.K.3
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0041050035
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(b) Maryanoff, B. E.; Greco, M. N.; Zhang, H. C.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc. 1995, 117, 1225.
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Maryanoff, B.E.1
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Brungs, P.H.8
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15
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0033588064
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and references therein
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For an excellent compilation of the leading stereospecific and asymmetric approaches to α-hydroxy-β-amino acids and amides, see: Wasserman, H. H.; Xia, M.; Jorgensen, M. R.; Curtis, E. A. Tetrahedron Lett 1999, 40, 6163 and references therein.
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Tetrahedron Lett
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Wasserman, H.H.1
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16
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0025050730
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See refs 4a, 5a, 7, 8, 9b,c and Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kuboto, T.; Umeyama, H.; Kiso, Y. J. Med. Chem. 1990, 33, 2707.
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Iizuka, K.1
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Umeyama, H.6
Kiso, Y.7
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20
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0029093733
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(a) Brady S. F.; Sisko, J. T.; Stauffer, K. J.; Colton, C. D.; Qui, H.; Lewis, S. D.; Ng, A. S.; Shafer, J. A.; Bogusky, M. J.; Veber D. F.; Nutt, R. F. Bioorg. Med. Chem. 1995, 3, 1063.
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Brady, S.F.1
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Lewis, S.D.6
Ng, A.S.7
Shafer, J.A.8
Bogusky, M.J.9
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Nutt, R.F.11
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21
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0026677967
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(b) Iwanowicz, E. J., Lin, J.; Roberts, D. G. M.; Michel, I, M.; Seiler, S. M. Bioorg. Med. Chem. Lett. 1992, 2, 1607.
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Iwanowicz, E.J.1
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22
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(a) Minami, N. K.; Reiner, J. E.; Semple, J. E. Bioorg. Med. Chem. Lett 1999, 9, 2625.
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Bioorg. Med. Chem. Lett
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Minami, N.K.1
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23
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0033593971
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(b) Reiner, J. E.; Lim-Wilby, M. S.; Brunck, T. K.; Uong, T. H.; Goldman, E. A.; Abelman, M. A.; Nutt, R. F.; Semple. J. E.; Tamura S. Y. Bioorg. Med. Chem. Lett. 1999, 9, 895.
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Bioorg. Med. Chem. Lett.
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Reiner, J.E.1
Lim-Wilby, M.S.2
Brunck, T.K.3
Uong, T.H.4
Goldman, E.A.5
Abelman, M.A.6
Nutt, R.F.7
Semple, J.E.8
Tamura, S.Y.9
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25
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0034678834
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(a) Tamura, S. Y.; Levy, O. E.; Reiner, J. E.; Uong, T. H.; Goldman, E. A.; Brunck, T. K.; Semple, J. E. Bioorg. Med. Chem. Lett. 2000, 10, 745.
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Bioorg. Med. Chem. Lett.
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Tamura, S.Y.1
Levy, O.E.2
Reiner, J.E.3
Uong, T.H.4
Goldman, E.A.5
Brunck, T.K.6
Semple, J.E.7
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0033590270
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(b) Ho, J. Z.; Levy, O. E.; Gibson, T. S.; Nguyen, K.; Semple, J. E. Bioorg. Med. Chem. Lett. 1999, 9, 3459.
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Bioorg. Med. Chem. Lett.
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Ho, J.Z.1
Levy, O.E.2
Gibson, T.S.3
Nguyen, K.4
Semple, J.E.5
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0034194355
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Tamura, S. Y.; Weinhouse, M. I.; Roberts, C. A.; Goldman, E. A.; Masukawa, K.; Anderson, S. M.; Cohen, C. R.; Bradbury, A. E.; Bernadino, V. T.; Dixon, S. A.; Ma, M. G.; Nolan, T. G.; Brunck, T. K. Bioorg. Med. Chem. Lett. 2000, 10, 983.
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Bioorg. Med. Chem. Lett.
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Tamura, S.Y.1
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Masukawa, K.5
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Cohen, C.R.7
Bradbury, A.E.8
Bernadino, V.T.9
Dixon, S.A.10
Ma, M.G.11
Nolan, T.G.12
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28
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0034678789
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and references therein
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Han, W.; Hu, Z.; Jiang, X.; Decicco, C. P. Bioorg. Med. Chem. Lett 2000, 10, 711 and references therein.
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Bioorg. Med. Chem. Lett
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Han, W.1
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Decicco, C.P.4
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0041050027
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Ugi, I., Ed.; Academic Press: New York
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(c) Ugi, I. in Isonitrile Chemistry; Ugi, I., Ed.; Academic Press: New York, 1971, Chapter 7.
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Isonitrile Chemistry
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Ugi, I.1
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(e) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
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(f) Ziegler, T.; Kaisers, H. J.; Schlomer, R.; Koch, C. Tetrahedron 1999, 55, 8397.
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Tetrahedron
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Ziegler, T.1
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Koch, C.4
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35
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84981758187
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Aqueous mineral acid-catalyzed versions
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(a) Aqueous mineral acid-catalyzed versions: Hagedorn, I.; Eholzer, U. Chem. Ber. 1965, 98, 936.
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(1965)
Chem. Ber.
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, pp. 936
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Hagedorn, I.1
Eholzer, U.2
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36
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84982336930
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3 to directly produce α-hydroxyamides
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3 to directly produce α-hydroxyamides: Muller, E.; Zeeh, B. Liebigs Ann. Chem. 1966, 696, 72.
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(1966)
Liebigs Ann. Chem.
, vol.696
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Muller, E.1
Zeeh, B.2
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33751385281
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4 activation
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4 activation: Carofiglio, T.; Cozzi, P. G.; Floriani, C.; Chiesa-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 2726.
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Organometallics
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Carofiglio, T.1
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Chiesa-Villa, A.4
Rizzoli, C.5
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84985648238
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(f) Seebach, D.; Adam, G.; Gees, T.; Schiess, M.; Weigand, W. Chem. Ber. 1988, 121, 507.
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Chem. Ber.
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Seebach, D.1
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Weigand, W.5
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41
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0019809851
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Passerini reaction of simple aldehydes and ketones with TFA and pyridine: Lumma, W. J. Org. Chem. 1981, 46, 3668.
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J. Org. Chem.
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Lumma, W.1
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0034716554
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(a) Myers, A. G.; Zhong, B.; Movassaghi, M.; Rung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359.
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Tetrahedron Lett.
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Myers, A.G.1
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46
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(e) Fehrentz, J. A.; Pothion, C.; Califano, J. C; Loffet, A.; Martinez, J. Tetrahedron Lett. 1994, 35, 9031.
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Fehrentz, J.A.1
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47
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0040455986
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note
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4, filtered, and concentrated. The crude product was either recrystallized or purified by flash column chromatography on silica gel using ethyl acetate/hexane or dichloromethane/methanol gradient systems. Pure products were obtained as either nearly colorless solids or as colorless to pale yellow viscous oils.
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48
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0041050020
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Minneapolis, MN, June 26-July 1
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Levy, O. E.; Nguyen, K.; Owens, T. D.; Semple, J. E. 16th American Peptide Symposium, Minneapolis, MN, June 26-July 1, 1999; P.6653.
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(1999)
16th American Peptide Symposium
, pp. 6653
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Levy, O.E.1
Nguyen, K.2
Owens, T.D.3
Semple, J.E.4
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49
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85087227548
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note
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R = 14.0 min (Chiracel AD column: 2-propanol, hexane 10-30% gradient; 0.5 mL/min flow rate).
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50
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0029803557
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Semple, J. E.; Rowley, D. C.; Brunck, T. K.; Ha-Uong, T.; Minami, N. K.; Owens, T. D.; Tamura, S. Y.; Goldman, E. A.; Siev, D. V.; Ardecky, R. J.; Carpenter, S. H.; Ge, Y.; Richard, B. M.; Nolan, T. G.; Håkanson, K.; Tulinsky, A.; Nutt, R. F.; Ripka, W. C. J. Med. Chem. 1996, 39, 4531.
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(1996)
J. Med. Chem.
, vol.39
, pp. 4531
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Semple, J.E.1
Rowley, D.C.2
Brunck, T.K.3
Ha-Uong, T.4
Minami, N.K.5
Owens, T.D.6
Tamura, S.Y.7
Goldman, E.A.8
Siev, D.V.9
Ardecky, R.J.10
Carpenter, S.H.11
Ge, Y.12
Richard, B.M.13
Nolan, T.G.14
Håkanson, K.15
Tulinsky, A.16
Nutt, R.F.17
Ripka, W.C.18
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