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4
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0031019142
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Pettit, G. R.; McNulty, J.; Herald, D. L.; Doubek, D. L.; Chapuis, J. C.; Schmidt, J. M.; Tackett, L. P.; Boyd, M. R. J. Nat. Prod 1997, 60, 180.
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Pettit, G.R.1
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Herald, D.L.3
Doubek, D.L.4
Chapuis, J.C.5
Schmidt, J.M.6
Tackett, L.P.7
Boyd, M.R.8
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5
-
-
33846047483
-
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50 of 0.7 μM against the glioblastoma cancer cell line CNXF 498NL, while (+)-1 was inactive. See: Zöllinger, M.; Kelter, G.; Fiebig, H.-H.; Lindel, T. Bioorg. Med. Chem. Lett. 2007, 17, 346.
-
50 of 0.7 μM against the glioblastoma cancer cell line CNXF 498NL, while (+)-1 was inactive. See: Zöllinger, M.; Kelter, G.; Fiebig, H.-H.; Lindel, T. Bioorg. Med. Chem. Lett. 2007, 17, 346.
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7
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17644414184
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Jacquot, D. E. N.; Zöllinger, M.; Lindel, T. Angew. Chem. Int. Ed. 2005, 44, 2295.
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Jacquot, D.E.N.1
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Lindel, T.3
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8
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0037100005
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Wiese, K. J.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 2002, 43, 5135.
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Wiese, K.J.1
Yakushijin, K.2
Horne, D.A.3
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10
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8744221400
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Chung, R.; Yu, E.; Incarvito, C. D.; Austin, D. J. Org. Lett. 2004, 6, 3881.
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Chung, R.1
Yu, E.2
Incarvito, C.D.3
Austin, D.J.4
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11
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34347214018
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Lu, J.; Tan, X.; Chen, C. J. Am. Chem. Soc. 2007, 129, 7768.
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Lu, J.1
Tan, X.2
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12
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33845528316
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Zöllinger, M.; Mayer, P.; Lindel, T. J. Org. Chem. 2006, 71, 9431.
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Zöllinger, M.1
Mayer, P.2
Lindel, T.3
-
13
-
-
0015857556
-
-
Compound 4 can be obtained by alkaline hydrolysis of the corresponding trichloromethylketone. See: Bailey, D. M.; Johnson, R. E. J. Med. Chem. 1973, 16, 1300.
-
Compound 4 can be obtained by alkaline hydrolysis of the corresponding trichloromethylketone. See: Bailey, D. M.; Johnson, R. E. J. Med. Chem. 1973, 16, 1300.
-
-
-
-
14
-
-
35649006888
-
-
CCDC-623847 (12) and CCDC-623846 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk].
-
CCDC-623847 (12) and CCDC-623846 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk].
-
-
-
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17
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4544264241
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Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. J. Org. Chem. 1985, 50, 5365.
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Fioravanti, S.1
Loreto, M.A.2
Pellacani, L.3
Tardella, P.A.4
-
18
-
-
33947087514
-
-
(a) Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Org. Chem. 1973, 38, 26.
-
(1973)
J. Org. Chem
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, pp. 26
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Burgess, E.M.1
Penton, H.R.2
Taylor, E.A.3
-
19
-
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0000010296
-
-
(b) Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Am. Chem. Soc. 1970, 92, 5224.
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-
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Burgess, E.M.1
Penton, H.R.2
Taylor, E.A.3
-
21
-
-
35648981108
-
-
Compound, )-16: [α]D25 +46.1 (c 1.2 mg/10.0 mL, MeOH, TLC (silica, EtOAc, Rf, 0.83. 1H NMR (600 MHz, CDCl3, δ, 1.40 (t, 3 H, 3J, 7.1 Hz, OCH2CH3, 2.42 (s, 3 H, ArCH3, 2.90-3.00 (m, 2 H, CCH2, 3.63 (dd, 1 H, 2J, 11.7 Hz, 3J, 9.9 Hz, NCHH, 4.12-4.18 (m, 1 H, CHBr, 4.42 (dq, 1 H, 2J, 11.5 Hz, 3J, 7.1 Hz, OCHH, 4.44 (dq, 1 H, 2J, 11.5 Hz, 3J, 7.1 Hz, OCHH, 4.53 (dd, 1 H, 2J, 11.7 Hz, 3J, 7.5 Hz, NCHH, 6.05 (s, 1 H, NCHN, 6.36 (dd, 1 H, 3J, 3.6, 3.1 Hz, CHCHCHN, 6.87 (dd, 1 H, 3J, 2.7 Hz, 4J, 1.6 Hz, CHCHCHN, 7.07 dd, 1 H, 3J, 3.9 Hz, 4
-
7S + H]: 553.0393; found: 553.0375.
-
-
-
-
22
-
-
35648988025
-
-
2 has rarely been reported: (a) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
-
2 has rarely been reported: (a) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
-
-
-
-
23
-
-
0002398754
-
-
(b) Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Lett. 1994, 379.
-
(1994)
Chem. Lett
, pp. 379
-
-
Ogawa, A.1
Nanke, T.2
Takami, N.3
Sumino, Y.4
Ryu, I.5
Sonoda, N.6
-
24
-
-
35649004440
-
-
Compound 17 had also been obtained as the (+)-enantiomer by Romo (ref. 5) and as the racemate by Austin (ref. 9).
-
Compound 17 had also been obtained as the (+)-enantiomer by Romo (ref. 5) and as the racemate by Austin (ref. 9).
-
-
-
-
25
-
-
35649017706
-
-
Compound, )-1: [α]D20 -75.7 (c 0.14 mg/mL, MeOH, TLC (silica, MeOH-CHCl3, 1:9, R f, 0.52. 1H NMR (600 MHz, DMSO-d6, δ, 1.95-2.00 (m, 1 H, NCHHCHH, 2.08-2.15 (m, 2 H, NCHHCHHCHH, 2.27-2.33 (m, 1 H, NCHHCHHCHH, 3.40-3.45 (m, 1 H, NCHH, 3.54-3.57 (m, 1 H, NCHH, 5.98 (s, 1 H, NCHN, 6.91 (s, 1 H, CBrCH, 7.97 (s, 1 H, NH, 8.26 (s, 1 H, NH, 13C NMR (150 MHz, DMSO-d6, δ, 18.8 (NCH2CH 2, 39.7 (CCH2, 44.1 (NCH2, 68.6 (NCHN, 78.9 (CCH2, 101.0 (CBrCH, 105.5 (NCBr, 113.7 (CBrCH, 125.3 (CBrCHC, 154.0 [N(CO)N, 157.8 [N(CO, MS (ESI, FTMS, m/z, 389/391/393 (40.9/100/39.1, M, H, CD (MeOH, λmax Δε, 260 nm, 1.1, tr, sh, 233, 2
-
+]: 388.9249; found: 388.9255.
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-
-
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