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1
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0009109864
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See, for example, clausenamide:;, Dysidamide:; Tetrahedron Lett. 1988, 29, 3863-3864 Lactacystin:; J. Antibiot. 1991, 44, 117-118 anchinopeptolides:; J. Nat. Prod. 1994, 57, 1227-1233 Salinosporamide:; Angew. Chem., Int. Ed. 2003, 42, 355-357 Berkeleyamides:; J. Nat. Prod. 2008, 71, 856-860
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See, for example, clausenamide: Yang, M.; Chen, Y.; Huang, L. Phytochemistry 1988, 27, 445-450 Dysidamide: Gebreyesus, T.; Yosief, T.; Carmely, S.; Kashman, Y. Tetrahedron Lett. 1988, 29, 3863-3864 Lactacystin: Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118 anchinopeptolides: Casapullo, A.; Minale, L.; Zollo, F.; Lavayre, J. J. Nat. Prod. 1994, 57, 1227-1233 Salinosporamide: Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355-357 Berkeleyamides: Stierle, A. A.; Stierle, D. B.; Patacini, B. J. Nat. Prod. 2008, 71, 856-860
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(1988)
Phytochemistry
, vol.27
, pp. 445-450
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Yang, M.1
Chen, Y.2
Huang, L.3
Gebreyesus, T.4
Yosief, T.5
Carmely, S.6
Kashman, Y.7
Omura, S.8
Matsuzaki, K.9
Fujimoto, T.10
Kosuge, K.11
Furuya, T.12
Fujita, S.13
Nakagawa, A.14
Casapullo, A.15
Minale, L.16
Zollo, F.17
Lavayre, J.18
Feling, R.H.19
Buchanan, G.O.20
Mincer, T.J.21
Kauffman, C.A.22
Jensen, P.R.23
Fenical, W.24
Stierle, A.A.25
Stierle, D.B.26
Patacini, B.27
more..
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2
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0347656946
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Guntern, A.; Ioset, J. R.; Queiroz, E. F.; Sandor, P.; Foggin, C. M.; Hostettmann, K. J. Nat. Prod. 2003, 66, 1550-1553
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(2003)
J. Nat. Prod.
, vol.66
, pp. 1550-1553
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Guntern, A.1
Ioset, J.R.2
Queiroz, E.F.3
Sandor, P.4
Foggin, C.M.5
Hostettmann, K.6
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3
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0028472709
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Kock, N. D.; Goedegebuure, S. A.; Lane, E. P.; Lucke, V.; Tyrrell, D.; Kock, M. D. J. Wildl. Dis. 1994, 30, 432-5
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(1994)
J. Wildl. Dis.
, vol.30
, pp. 432-435
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Kock, N.D.1
Goedegebuure, S.A.2
Lane, E.P.3
Lucke, V.4
Tyrrell, D.5
Kock, M.D.6
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4
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2342454320
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Okazaki, Y.; Ishihara, A.; Nishioka, T.; Iwamura, H. Tetrahedron 2004, 60, 4765-4771
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(2004)
Tetrahedron
, vol.60
, pp. 4765-4771
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Okazaki, Y.1
Ishihara, A.2
Nishioka, T.3
Iwamura, H.4
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5
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34248563404
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Okazaki, Y.; Ishizuka, A.; Ishihara, A.; Nishioka, T.; Iwamura, H. J. Org. Chem. 2007, 72, 3830-3839
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(2007)
J. Org. Chem.
, vol.72
, pp. 3830-3839
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Okazaki, Y.1
Ishizuka, A.2
Ishihara, A.3
Nishioka, T.4
Iwamura, H.5
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8
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78650265633
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3SiH was used for larger scale work
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3SiH was used for larger scale work.
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9
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34248563404
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Okazaki, Y. I., A.; Ishihara, A.; Nishioka, T.; Iwamura, H. J. Org. Chem. 2007, 27, 3830-3839
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(2007)
J. Org. Chem.
, vol.27
, pp. 3830-3839
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Okazaki, Y.I.A.1
Ishihara, A.2
Nishioka, T.3
Iwamura, H.4
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10
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78650270638
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We were unable to contact Prof. Hostettmann (ref 2) to obtain an authentic sample for direct comparison
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We were unable to contact Prof. Hostettmann (ref 2) to obtain an authentic sample for direct comparison.
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11
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78650277625
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the isolation paper (ref 2), the configuration of the aromatic and carboxamide substituents on the core lactam are described as "cis", though they are depicted as trans (anti). We assumed this to be a typographical error. Our synthesis, which relies on methods to prepare the anticonfigured lactam (previuosly demonstrated by X-ray crystallography, see ref 5a), established that the configuration is anti. Attempts to crystallize 21, heliotropamide and several derivatives thereof were unsuccessful
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In the isolation paper (ref 2), the configuration of the aromatic and carboxamide substituents on the core lactam are described as "cis", though they are depicted as trans (anti). We assumed this to be a typographical error. Our synthesis, which relies on methods to prepare the anticonfigured lactam (previuosly demonstrated by X-ray crystallography, see ref 5a), established that the configuration is anti. Attempts to crystallize 21, heliotropamide and several derivatives thereof were unsuccessful.
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12
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0000337713
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1H NMR shifts of the vinylic proton in related alkylidene γ-lactams and lactones is generally 0.4-0.6 ppm higher upfield for the Z isomer when compared to the E isomer. See
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1H NMR shifts of the vinylic proton in related alkylidene γ-lactams and lactones is generally 0.4-0.6 ppm higher upfield for the Z isomer when compared to the E isomer. See: Lewis, F. D.; Oxman, J. D.; Gibson, L. L.; Hampsch, H. L.; Quillen, S. L. J. Am. Chem. Soc. 1986, 108, 3005-3015
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(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 3005-3015
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Lewis, F.D.1
Oxman, J.D.2
Gibson, L.L.3
Hampsch, H.L.4
Quillen, S.L.5
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13
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0029079187
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Ezquerra, J. P., C.; Yruretagoyena, B.; Rubio, A.; Carreno, M. C.; Escribano, A.; Ruano, J. L. G. J. Org. Chem. 1995, 60, 2925-2930
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J. Org. Chem.
, vol.60
, pp. 2925-2930
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Ezquerra, J.P.C.1
Yruretagoyena, B.2
Rubio, A.3
Carreno, M.C.4
Escribano, A.5
Ruano, J.L.G.6
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14
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0038334973
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Kang, J.-H. C., H.-E.; Kim, S. Y.; Kim, Y.; Lee, J.; Lewin, N. E.; Pearce, L. V.; Blumberg, P. B.; Marquez, V. E. Bioorg. Med. Chem. 2003, 11, 2529-2539
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(2003)
Bioorg. Med. Chem.
, vol.11
, pp. 2529-2539
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Kang, J.-H.C.H.-E.1
Kim, S.Y.2
Kim, Y.3
Lee, J.4
Lewin, N.E.5
Pearce, L.V.6
Blumberg, P.B.7
Marquez, V.E.8
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