-
1
-
-
3843072211
-
-
(a) Weber, A. J. Med. Chem. 2004, 47, 4135.
-
(2004)
J. Med. Chem
, vol.4
, Issue.7
, pp. 4135
-
-
Weber, A.1
-
4
-
-
33847021133
-
-
(a) Sheehan, S. M.; Mest, H.; Watson, B. M.; Klimkowski, V. J.; Timm, D. E.; Cauvin, A.; Parsons, S. H.; Shi, Q.; Canada, E. J.; Wiley, M. R.; Ruehter, G.; Evers, B.; Petersen, S.; Blaszczak, L. C.; Pulley, S. R.; Margolis, B. J.; Wishart, G. N.; Renson, B.; Hankotius, D.; Mohr, M.; Zechel, J.; Kalbfleisch, J. M.; Dingess-Hammond, E. A.; Boelke, A.; Weichert, A. G. Bioorg. Med. Chem. Lett. 2007, 17, 1765.
-
(2007)
Bioorg. Med. Chem. Lett
, vol.1
, Issue.7
, pp. 1765
-
-
Sheehan, S.M.1
Mest, H.2
Watson, B.M.3
Klimkowski, V.J.4
Timm, D.E.5
Cauvin, A.6
Parsons, S.H.7
Shi, Q.8
Canada, E.J.9
Wiley, M.R.10
Ruehter, G.11
Evers, B.12
Petersen, S.13
Blaszczak, L.C.14
Pulley, S.R.15
Margolis, B.J.16
Wishart, G.N.17
Renson, B.18
Hankotius, D.19
Mohr, M.20
Zechel, J.21
Kalbfleisch, J.M.22
Dingess-Hammond, E.A.23
Boelke, A.24
Weichert, A.G.25
more..
-
5
-
-
34548835778
-
-
(b) Kowalchick, J. E.; Letting, B.; Pryor, K. D.; Marsilio, F.; Wu, J. K.; He, H.; Lyons, K. A.; Eiermann, G. J.; Petrov, A.; Scapin, G.; Patel, R. A.; Thornberry, N. A.; Weber, A. E.; Kim, D. Bioorg. Med. Chem. Lett. 2007, 17, 5934.
-
(2007)
Bioorg. Med. Chem. Lett
, vol.1
, Issue.7
, pp. 5934
-
-
Kowalchick, J.E.1
Letting, B.2
Pryor, K.D.3
Marsilio, F.4
Wu, J.K.5
He, H.6
Lyons, K.A.7
Eiermann, G.J.8
Petrov, A.9
Scapin, G.10
Patel, R.A.11
Thornberry, N.A.12
Weber, A.E.13
Kim, D.14
-
6
-
-
34247869769
-
-
(c) Luebbers, T.; Boehringer, M.; Gobbi, L.; Hennig, M.; Hunziker, D.; Kuhn, B.; Loeffler, B.; Mattei, P.; Narquizian, R.; Peters, J.; Ruff, Y.; Wessel, H. P.; Wyss, P. Bioorg. Med. Chem. Lett. 2007, 17, 2966.
-
(2007)
Bioorg. Med. Chem. Lett
, vol.1
, Issue.7
, pp. 2966
-
-
Luebbers, T.1
Boehringer, M.2
Gobbi, L.3
Hennig, M.4
Hunziker, D.5
Kuhn, B.6
Loeffler, B.7
Mattei, P.8
Narquizian, R.9
Peters, J.10
Ruff, Y.11
Wessel, H.P.12
Wyss, P.13
-
7
-
-
34248999413
-
-
(d) Feng, J.; Zhang, Z.; Wallace, M. B.; Stafford, J. A.; Kaldor, S. W.; Kassel, D. B.; Navre, M.: Shi, L.; Skene. R. J.; Asakawa, T.; Takeuchi, K.; Xu, R.; Webb, D. R.; Gwaltney, S. L. J. Med. Chem. 2007, 50, 2297.
-
(2007)
J. Med. Chem
, vol.5
, Issue.0
, pp. 2297
-
-
Feng, J.1
Zhang, Z.2
Wallace, M.B.3
Stafford, J.A.4
Kaldor, S.W.5
Kassel, D.B.6
Navre, M.7
Shi, L.8
Skene, R.J.9
Asakawa, T.10
Takeuchi, K.11
Xu, R.12
Webb, D.R.13
Gwaltney, S.L.14
-
8
-
-
33947720282
-
-
(e) Yoshida, T.; Sakashita, H.; Akahoshi, F.; Hayashi, Y. Bioorg. Med. Chem. Lett. 2007, 17, 2618.
-
(2007)
Bioorg. Med. Chem. Lett
, vol.1
, Issue.7
, pp. 2618
-
-
Yoshida, T.1
Sakashita, H.2
Akahoshi, F.3
Hayashi, Y.4
-
9
-
-
34247204289
-
-
(f) Pei, Z.; Li, X.; Von, G.; Thomas, W; Longeneck, K.; Pireh, D.; Stewart, K. D.; Backes, B. J.; Lai, C.; Lubben, T. H.; Ballaron, S. J.; Beno, D. W. A.; Kempf-Grote, A. J.; Sham, H. L.; Trevillyan, J. M. J. Med. Chem. 2007, 50, 1983.
-
(1983)
J. Med. Chem
, vol.2007
, Issue.5
-
-
Pei, Z.1
Li, X.2
Von, G.3
Thomas, W.4
Longeneck, K.5
Pireh, D.6
Stewart, K.D.7
Backes, B.J.8
Lai, C.9
Lubben, T.H.10
Ballaron, S.J.11
Beno, D.W.A.12
Kempf-Grote, A.J.13
Sham, H.L.14
Trevillyan, J.M.15
-
10
-
-
33846904812
-
-
(g) Tran, T.; Quan, C.; Edosada, C. Y.; Mayeda, M.: Wiesmann, C.; Sutherlin, D.; Wolf, B. B. Bioorg. Med. Chem. Lett. 2007, 17, 1438.
-
(2007)
Bioorg. Med. Chem. Lett
, vol.1
, Issue.7
, pp. 1438
-
-
Tran, T.1
Quan, C.2
Edosada, C.Y.3
Mayeda, M.4
Wiesmann, C.5
Sutherlin, D.6
Wolf, B.B.7
-
11
-
-
58149153546
-
-
Blaszczak, L. C.; Mathes, B. M.; Pulley, S. R.; Robertson, M. A.; Sheehan, S. M.: Shi. Q.; Watson, B. M.; Wiley, M. R. WO 2007/015767 Al, 2007.
-
Blaszczak, L. C.; Mathes, B. M.; Pulley, S. R.; Robertson, M. A.; Sheehan, S. M.: Shi. Q.; Watson, B. M.; Wiley, M. R. WO 2007/015767 Al, 2007.
-
-
-
-
14
-
-
58149147965
-
-
Eur. Pat. Appl. EP934923A1
-
(c) Satoh. H.; Turk, G. H. Eur. Pat. Appl. EP934923A1, 1999.
-
(1999)
-
-
Satoh, H.1
Turk, G.H.2
-
16
-
-
30744473984
-
-
(e) Yin, J.; Huffman, M. A.; Conrad, K. M.; Armstrong, J. D. J. Org. Chem. 2006, 71, 840.
-
(2006)
J. Org. Chem
, vol.7
, Issue.1
, pp. 840
-
-
Yin, J.1
Huffman, M.A.2
Conrad, K.M.3
Armstrong, J.D.4
-
17
-
-
0037154749
-
-
(a) Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045.
-
(2002)
J. Org. Chem
, vol.6
, Issue.7
, pp. 1045
-
-
Hoffman, R.V.1
Maslouh, N.2
Cervantes-Lee, F.3
-
18
-
-
0347367042
-
-
(b) Vabeno, J.; Brisander, M.; Lejon, T.; Luthman, K. J. Org. Chem. 2002, 67, 9186.
-
(2002)
J. Org. Chem
, vol.6
, Issue.7
, pp. 9186
-
-
Vabeno, J.1
Brisander, M.2
Lejon, T.3
Luthman, K.4
-
19
-
-
58149170864
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Ketones 9a and 9b were observed as a mixture of ketone and enone forms in NMR.
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Ketones 9a and 9b were observed as a mixture of ketone and enone forms in NMR.
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20
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0037064525
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-
A similar predeprotonation protocol has been reported in the synthesis of α-(N-Boc-amino)ketones from α-(N-Boc-amino)Weinreb amide: Liu, J.; Ikemoto, N.; Petrillo, D.; Armstrong, J. D Tetrahedron Lett. 2002, 43, 8223.
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A similar predeprotonation protocol has been reported in the synthesis of α-(N-Boc-amino)ketones from α-(N-Boc-amino)Weinreb amide: Liu, J.; Ikemoto, N.; Petrillo, D.; Armstrong, J. D Tetrahedron Lett. 2002, 43, 8223.
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-
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The preparation of dianion-8 was described in the subsequent text in the Scheme 4 approach.
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The preparation of dianion-8 was described in the subsequent text in the Scheme 4 approach.
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-
-
22
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-
0028362882
-
A Bioorg
-
(a) Kaldor, S. W.; Hammond, M.; Dressman, B. A.; Fritz, J. E.; Crowell, T. A.; Hermann, R. A Bioorg. Med. Chem. Lett. 1994, 4, 1385.
-
(1994)
Med. Chem. Lett
, vol.4
, pp. 1385
-
-
Kaldor, S.W.1
Hammond, M.2
Dressman, B.A.3
Fritz, J.E.4
Crowell, T.A.5
Hermann, R.6
-
23
-
-
0027164896
-
-
(b) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217.
-
(1993)
Tetrahedron Lett
, vol.3
, Issue.4
, pp. 5217
-
-
Bohnstedt, A.C.1
Prasad, J.V.N.V.2
Rich, D.H.3
-
27
-
-
84985516476
-
-
(a) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141.
-
(1987)
Angew. Chem., Int. Ed. Engl
, vol.2
, Issue.6
, pp. 1141
-
-
Reetz, M.T.1
Drewes, M.W.2
Schmitz, A.3
-
28
-
-
0025310964
-
-
(b) Mikami, K.; Kaneko, M.; Loh, T.; Masahiro, T.; Nakai, T. Tetrahedron Lett. 1990, 31, 3909.
-
(1990)
Tetrahedron Lett
, vol.3
, Issue.1
, pp. 3909
-
-
Mikami, K.1
Kaneko, M.2
Loh, T.3
Masahiro, T.4
Nakai, T.5
-
31
-
-
0026084964
-
-
(e) DeCamp, A. E.; Kawaguchi, A. T.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1991, 32, 1867.
-
(1991)
Tetrahedron Lett
, vol.3
, Issue.2
, pp. 1867
-
-
DeCamp, A.E.1
Kawaguchi, A.T.2
Volante, R.P.3
Shinkai, I.4
-
32
-
-
0001430378
-
-
(f) Barluenga, J.; Baragana, B.; Concellon, J. M. J. Org. Chem. 1995, 60, 6696.
-
(1995)
J. Org. Chem
, vol.6
, Issue.0
, pp. 6696
-
-
Barluenga, J.1
Baragana, B.2
Concellon, J.M.3
-
33
-
-
0028964460
-
-
(g) Beaulieu, P. L.; Wrnic, D.; Jean-Simon, D.; Yvan, G. Tetrahedron Lett. 1995, 36, 3317.
-
(1995)
Tetrahedron Lett
, vol.3
, Issue.6
, pp. 3317
-
-
Beaulieu, P.L.1
Wrnic, D.2
Jean-Simon, D.3
Yvan, G.4
-
34
-
-
85004804006
-
-
To fund the lab development of the subsequent steps, we also developed the synthesis of amino ester 14. The synthesis involved a classical Erlenmeyer condensation of 2,4-difluorobenzyaldehyde with N-acetyl glycine, followed by azlactone ring-opening to afford the corresponding dehydroamino ester. Amino ester 14 was further obtained from the dehydramino ester in >99% ee through enzyme resolution or asymmetric hydrogenation approach. For references on the synthesis of amino acids and derivatives, see: Roper, J. M.; Bauer, D. P. Synthesis 1983, 1041.
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(a) To fund the lab development of the subsequent steps, we also developed the synthesis of amino ester 14. The synthesis involved a classical Erlenmeyer condensation of 2,4-difluorobenzyaldehyde with N-acetyl glycine, followed by azlactone ring-opening to afford the corresponding dehydroamino ester. Amino ester 14 was further obtained from the dehydramino ester in >99% ee through enzyme resolution or asymmetric hydrogenation approach. For references on the synthesis of amino acids and derivatives, see: Roper, J. M.; Bauer, D. P. Synthesis 1983, 1041.
-
-
-
-
36
-
-
23044457042
-
-
(c) Boaz, N. W.; Large, S. E.; Ponasik, J. A.; Moore, M. K.; Barnette, T.; Nottingham, W. D. Org. Process Res. & Dev. 2005, 9, 472.
-
(2005)
Org. Process Res. & Dev
, vol.9
, pp. 472
-
-
Boaz, N.W.1
Large, S.E.2
Ponasik, J.A.3
Moore, M.K.4
Barnette, T.5
Nottingham, W.D.6
-
38
-
-
33947732100
-
-
Cativiela, C; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569.
-
(e) Cativiela, C; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569.
-
-
-
-
39
-
-
37049013519
-
-
(f) Humphrey, C. E.; Furegati, M.; Laumen, K.; Vecchia, L. L.; Leutert, T.; Muller-Hartwieg, J. C. D.: Vogtle, M. Org. Process Res. Dev. 2007, 11, 1069.
-
(2007)
Org. Process Res. Dev
, vol.1
, Issue.1
, pp. 1069
-
-
Humphrey, C.E.1
Furegati, M.2
Laumen, K.3
Vecchia, L.L.4
Leutert, T.5
Muller-Hartwieg, J.C.D.6
Vogtle, M.7
-
40
-
-
26044453018
-
-
(a) Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.: Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
-
(2005)
Bioorg. Med. Chem. Lett
, vol.1
, Issue.5
, pp. 4898
-
-
Lahm, G.P.1
Selby, T.P.2
Freudenberger, J.H.3
Stevenson, T.M.4
Myers, B.J.5
Seburyamo, G.6
Smith, B.K.7
Flexner, L.8
Clark, C.E.9
Cordova, D.10
-
41
-
-
0001391280
-
-
(b) Okada, E.; Kinomura, T; Higashiyama, Y.; Takeuchi, H.: Hojo, M. Heterocycles 1997, 46, 129.
-
(1997)
Heterocycles
, vol.4
, Issue.6
, pp. 129
-
-
Okada, E.1
Kinomura, T.2
Higashiyama, Y.3
Takeuchi, H.4
Hojo, M.5
-
42
-
-
0031493949
-
-
Liu, C.; Ng, J. S.; Behling, J. R.; Yen, C. H.; Campbell, A. L.; Fuzail, K. S.; Yonan, E. E.; Mehrotra, D. V. Org. Process Res. Dev. 1997, 1, 45.
-
(1997)
Org. Process Res. Dev
, vol.1
, pp. 45
-
-
Liu, C.1
Ng, J.S.2
Behling, J.R.3
Yen, C.H.4
Campbell, A.L.5
Fuzail, K.S.6
Yonan, E.E.7
Mehrotra, D.V.8
-
44
-
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58149162298
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Lower yield was due to the recovery of aldehyde starting material 12, which may be caused by the aldehyde enolization during the dianion 8 addition. The hypothesis was that the extra diisopropylamine might help suppress the enolization of the aldehyde.
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Lower yield was due to the recovery of aldehyde starting material 12, which may be caused by the aldehyde enolization during the dianion 8 addition. The hypothesis was that the extra diisopropylamine might help suppress the enolization of the aldehyde.
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-
48
-
-
0034669286
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-
(d) Xu, F.; Reamer, R. A.; Tillyer, R.; Cummins, J. M.; Grabowski, E. J. J.; Reider, P. J.; Collum, D. B.; Huffman, J. C. J. Am. Chem. Soc. 2000. 122, 11212.
-
(2000)
J. Am. Chem. Soc
, vol.12
, Issue.2
, pp. 11212
-
-
Xu, F.1
Reamer, R.A.2
Tillyer, R.3
Cummins, J.M.4
Grabowski, E.J.J.5
Reider, P.J.6
Collum, D.B.7
Huffman, J.C.8
-
49
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58149167338
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The FTIR instrument is a Mettler-Toledo ReactIR-4000 equippe with a DiComp diamond sensor, a liquid nitrogen cooled MCT detector. Software version ReactIR 3.0 is used.
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The FTIR instrument is a Mettler-Toledo ReactIR-4000 equippe with a DiComp diamond sensor, a liquid nitrogen cooled MCT detector. Software version ReactIR 3.0 is used.
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-
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-
50
-
-
0029019630
-
-
Ng, J. S.; Przybyla, C. A; Liu, C.; Yen, J. C.; Muellner, F. W.; Weyker, C. L. Tetrahedron 1995, 51, 6397.
-
Ng, J. S.; Przybyla, C. A; Liu, C.; Yen, J. C.; Muellner, F. W.; Weyker, C. L. Tetrahedron 1995, 51, 6397.
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