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1
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85030207967
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note
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1. This work was almost carried out at Hokkaido University.
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2
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0019258699
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2. (a) Omura, S.; Nakagawa, A.; Hashimoto, H.; Oiwa, R.; Iwai, Y.; Hirano, A.; Shibukawa, N.; Kojima, Y. J. Antibiotics 1980, 33, 1395-1396.
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J. Antibiotics
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Omura, S.1
Nakagawa, A.2
Hashimoto, H.3
Oiwa, R.4
Iwai, Y.5
Hirano, A.6
Shibukawa, N.7
Kojima, Y.8
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3
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0019832338
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(b) Nakagawa, A.; Iwai, Y.; Hashimoto, H.; Miyazaki, N.; Oiwa, R.; Takahashi, Y.; Hirano, A.; Shibukawa, N.; Kojima, Y.; Omura, S. ibid. 1981, 34, 1408-1415.
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(1981)
J. Antibiotics
, vol.34
, pp. 1408-1415
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-
Nakagawa, A.1
Iwai, Y.2
Hashimoto, H.3
Miyazaki, N.4
Oiwa, R.5
Takahashi, Y.6
Hirano, A.7
Shibukawa, N.8
Kojima, Y.9
Omura, S.10
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4
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0030048051
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3. For biological activities and structures of benzastatins closely related to 1, see: (a) Kim, W.-G.; Kim, J.-P.; Kim, C.-J.; Lee, K.-H.; Yoo, I.-D. J. Antibiotics 1996, 49, 20-25.
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(1996)
J. Antibiotics
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, pp. 20-25
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Kim, W.-G.1
Kim, J.-P.2
Kim, C.-J.3
Lee, K.-H.4
Yoo, I.-D.5
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5
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0030053567
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(b) Kim, W.-G.; Kim, J.-P.; Yoo, I.-D. ibid. 1996, 49, 26-30.
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(1996)
J. Antibiotics
, vol.49
, pp. 26-30
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Kim, W.-G.1
Kim, J.-P.2
Yoo, I.-D.3
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8
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0025046452
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(b) Idem Tetrahedron 1990, 46, 4587-4594.
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(1990)
Tetrahedron
, vol.46
, pp. 4587-4594
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9
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0000345657
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6. For our preliminary communications of this work, see: (a) Morimoto, Y.; Oda, K.; Shirahama, H.; Matsumoto, T.; Omura, S. Chem. Lett. 1988, 909-912.
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Chem. Lett.
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Morimoto, Y.1
Oda, K.2
Shirahama, H.3
Matsumoto, T.4
Omura, S.5
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10
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0025183188
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(b) Morimoto, Y.; Matsuda, F.; Shirahama, H. Tetrahedron Lett. 1990, 31, 6031-6034.
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Morimoto, Y.1
Matsuda, F.2
Shirahama, H.3
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11
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0012045646
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(c) Idem Synlett 1991, 201-203.
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(1991)
Synlett
, pp. 201-203
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14
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84970626943
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9. For other synthetic approaches towards virantmycin (1), see: (a) Raner, K. D.; Skelton, B. W.; Ward, A. D.; White, A. H. Aust. J. Chem. 1990, 43, 609-616.
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Aust. J. Chem.
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Raner, K.D.1
Skelton, B.W.2
Ward, A.D.3
White, A.H.4
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16
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0000166661
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(c) De Silva, A. N.; Francis, C. L.; Ward, A. D. ibid. 1993, 46, 1657-1671.
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Aust. J. Chem.
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De Silva, A.N.1
Francis, C.L.2
Ward, A.D.3
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18
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0028785689
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(e) Williamson, N. M.; March, D. R.; Ward, A. D. Tetrahedron Lett. 1995, 36, 7721-7724.
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Tetrahedron Lett.
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, pp. 7721-7724
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Williamson, N.M.1
March, D.R.2
Ward, A.D.3
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23
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0000700393
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(e) Abramovitch, R. A.; Challand, S. R.; Yamada, Y. J. Org. Chem. 1975, 40, 1541-1547.
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Abramovitch, R.A.1
Challand, S.R.2
Yamada, Y.3
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24
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0017383827
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11. Inoue, S.; Takamatsu, N.; Kishi, Y. Yakugaku Zasshi 1977, 97, 553-557.
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Yakugaku Zasshi
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Inoue, S.1
Takamatsu, N.2
Kishi, Y.3
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27
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33845373924
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14. This phosphonate 16 was prepared from commercially available methyl bis(2,2,2-trifluoroethyl)phosphonoacetate by alkylation (NaH, EtI, DMSO, rt, 2 d, 85%). See: Marshall, J. A.; DeHoff, B. S.; Cleary, D. G. J. Org. Chem. 1986, 51, 1735-1741.
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Marshall, J.A.1
DeHoff, B.S.2
Cleary, D.G.3
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29
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33845281002
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16. For generation of aryl nitrene by photolysis of aryl azide, see: Shields, C. J.; Chrisope, D. R.; Schuster, G. B.; Dixon, A. J.; Poliakoff, M.; Turner, J. J. J. Am. Chem. Soc. 1987, 109, 4723-4726.
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Shields, C.J.1
Chrisope, D.R.2
Schuster, G.B.3
Dixon, A.J.4
Poliakoff, M.5
Turner, J.J.6
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30
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0000791380
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17. It is well known that a ring opening of aziridines proceeds with inversion like epoxides. See: (a) Paris, O. E.; Fanta, P. E. J. Am. Chem. Soc. 1952, 74, 3007-3010.
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Paris, O.E.1
Fanta, P.E.2
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31
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33947448382
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(b) Cromwell, N. H.; Hudson, G. V.; Wankel, R. A.; Vanderhorst, P. J. ibid. 1953, 75, 5384-5389.
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Cromwell, N.H.1
Hudson, G.V.2
Wankel, R.A.3
Vanderhorst, P.J.4
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33
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0001192078
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(d) Hammer, C. F.; Heller, S. R.; Craig, J. H. Tetrahedron 1972, 28, 239-253.
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Tetrahedron
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Hammer, C.F.1
Heller, S.R.2
Craig, J.H.3
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34
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0002211812
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18. (a) Node, M.; Nishide, K.; Sai, M.; Ichikawa, K.; Fuji, K.; Fujita, E. Chem. Lett. 1979, 97-98.
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Chem. Lett.
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Node, M.1
Nishide, K.2
Sai, M.3
Ichikawa, K.4
Fuji, K.5
Fujita, E.6
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35
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33847085007
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(b) Node, M.; Nishide, K.; Fuji, K.; Fujita, E. J. Org. Chem. 1980, 45, 4275-4277.
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Node, M.1
Nishide, K.2
Fuji, K.3
Fujita, E.4
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36
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0001537435
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19. (a) Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976, 98, 2674-2676.
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Hegedus, L.S.1
Allen, G.F.2
Waterman, E.L.3
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37
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33947093389
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(b) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. ibid. 1978, 100, 5800-5807.
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Hegedus, L.S.1
Allen, G.F.2
Bozell, J.J.3
Waterman, E.L.4
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39
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19644397969
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21. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616-5617.
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Corey, E.J.1
Gilman, N.W.2
Ganem, B.E.3
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40
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85030202638
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note
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22. Analogously, the protons involved in the pyrrolidine or piperidine ring moieties of 35-37 and 40-46 showed chemical shifts and coupling constants similar to those obtained for the protons in these ring systems of the corresponding model compounds 18-27. See experimental section.
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41
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84984929707
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and references cited therein
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23. For energetic investigations on ring inversion in cyclohexene and related molecules, see: Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969-10971 and references cited therein.
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Anet, F.A.L.1
Freedberg, D.I.2
Storer, J.W.3
Houk, K.N.4
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John Wiley & Sons, Inc.: New York
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24. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; John Wiley & Sons, Inc.: New York, 1967; Vol. 1, pp. 637-643.
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Fieser, L.F.1
Fieser, M.2
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