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Dolastatin 3 (2 thiazoles): Pettit, G. R.; Kamano, Y.; Holzapfel, C. W.; van Zyl, W. J.; Tuinman, A. A.; Herald, C. L.; Baczynskyj, L.; Schmidt, J. M. J. Am. Chem. Sue. 1987,109,7581.
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Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 236.
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Hamada, Y.1
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Hamada, Y.; Shibata, M.; Shioiri, T. Tetrahedron Lett. 1985, 26, 6501.
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Hamada, Y.1
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0021967530
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Ulicyclamide (1 oxazoline, 2 thiazoles): Schmidt, U.; Gleich, P. Angew. Chem., Int. Ed. Engl. 1985, 24, 569.
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Schmidt, U.1
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0041788104
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Ulithiacyclamide (2 oxazolines, 2 thiazoles): Kato, S.; Hamda, Y.; Shioiri, T. Tetrahedron Lett. 1986, 27, 2653.
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Kato, S.1
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85047669843
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Nakamura, M.; Shibata, T.; Nakane, K.; Nemoto, T.; Ojika, M.; Yamada, K. Tetrahedron Lett. 1995, 36, 5059.
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Yamada, K.6
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48
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0021048047
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Wasylyk, J. M.; Biskupiak, J. E; Costello, C. E.; Ireland, C. M. J. Org. Chem. 1983, 48, 4445. This activity was determined in L1210 cells.
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Wasylyk, J.M.1
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0025316403
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(a) Hawkins, C. J.; Lavin, M. F.; Marshall, K. A.; Brenk, A. L. v. d.; Watters, D. J. J. Med. Chem. 1990, 33, 1634.
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Watters, D.J.5
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50
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0024395134
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(b) Degnan, B. M.; Hawkins, C. J.; Lavin, M. F.; McCaffrey, E. J.; Parry, D. L.; Brenk, A. L. v. d.; Watters, D. J. J. Med. Chem. 1989, 32, 1349. This activity was determined in T24 cells.
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Degnan, B.M.1
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0019955047
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Ireland, C. M.; Durso, A. R.; Newman, R. A.; Hacker, M. P. J. Org. Chem. 1982, 47, 1807. This activity was determined in L1210 cells.
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Ireland, C.M.1
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(b) Dudash, J.; Jiang, J.; Mayer, S. C.; Joullie, M. M. Synth. Commun. 1993, 23, 349.
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(b) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
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57
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33847444846
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note
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13C NMR spectra of natural lissoclinamide 7. We thank Prof. D. Walters for providing us with copies of her data.
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-
-
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58
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0028258482
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For an example of the simultaneous formation of an oxazoline and a thiazoline using this methodology, see: Boden and Pattenden (ref 18). In the cyclopeptide area, the simultaneous formation of two oxazolines was reported by Shioiri et al. and Schmidt et al. (refs 13 and 14). For the simultaneous formation of multiple thiazolines or oxazolines in linear polyazoles, see: Parsons, R. L.; Heathcock, C. H. Tetrahedron Lett. 1994, 35, 1383.
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Parsons, R.L.1
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For comparison, see: Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938 and references cited therein.
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Boger, D.L.1
Zhou, J.2
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62
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33847451200
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The coordinates and a detailed discussion of the three-dimensional structure of lissoclinamide 7 will be reported elsewhere.
-
The coordinates and a detailed discussion of the three-dimensional structure of lissoclinamide 7 will be reported elsewhere.
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