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0011432222
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Dedicated to the memory of Prof. Henry C. Wu
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(1) Dedicated to the memory of Prof. Henry C. Wu
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2
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0023052241
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(2) (a) Nishizuka, Y. Science 1986, 233, 305.
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(1986)
Science
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, pp. 305
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Nishizuka, Y.1
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4
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0027536556
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(3) Bradshaw, D.; Hill, C. H.; Nixon, J. S.; Wilkinson, S. E. Agents Actions 1993, 38, 135.
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Agents Actions
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Bradshaw, D.1
Hill, C.H.2
Nixon, J.S.3
Wilkinson, S.E.4
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5
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0027239682
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(4) (a) Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452.
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(1993)
J. Am. Chem. Soc.
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Kulanthaivel, P.1
Hallock, Y.F.2
Boros, C.3
Hamilton, S.M.4
Janzen, W.P.5
Ballas, L.M.6
Loomis, C.R.7
Jiang, J.B.8
Katz, B.9
Steiner, J.R.10
Clardy, J.11
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6
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0028223687
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(b) Ohshima, S.; Yanagisawa, M.; Katoh, A.; Fujii, T.; Sano, T.; Matsukuma, S.; Furumai, T.; Fujiu, M; Watanabe, K.; Yokose, K.; Arisawa, M.; Okuda, T. J. Antibiotics 1994, 47, 639.
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J. Antibiotics
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Ohshima, S.1
Yanagisawa, M.2
Katoh, A.3
Fujii, T.4
Sano, T.5
Matsukuma, S.6
Furumai, T.7
Fujiu, M.8
Watanabe, K.9
Yokose, K.10
Arisawa, M.11
Okuda, T.12
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7
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0345664754
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(5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
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(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 5897
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Martínez, L.E.1
Leighton, J.L.2
Carsten, D.H.3
Jacobsen, E.N.4
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8
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0030070775
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(5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
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(1996)
J. Org. Chem.
, vol.61
, pp. 389
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Leighton, J.L.1
Jacobsen, E.N.2
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9
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0030605102
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(5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 7937
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Schaus, S.E.1
Jacobsen, E.N.2
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10
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0039094109
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(5) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. For recent synthetic applications, see Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389; Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937; and Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963.
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(1996)
J. Org. Chem.
, vol.61
, pp. 7963
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Martínez, L.E.1
Nugent, W.A.2
Jacobsen, E.N.3
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11
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0028090343
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(6) The total synthesis has been reported by three groups: (a) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402.
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 8402
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Nicolaou, K.C.1
Bunnage, M.E.2
Koide, K.3
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12
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0029989687
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and references contained therein
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(b) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1996, 61, 4572, and references contained therein.
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(1996)
J. Org. Chem.
, vol.61
, pp. 4572
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Lampe, J.W.1
Hughes, P.F.2
Biggers, C.K.3
Smith, S.H.4
Hu, H.5
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13
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37049080108
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(c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
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(1995)
J. Chem. Soc. Perkin Trans I
, pp. 2355
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Adams, C.P.1
Fairway, S.M.2
Hardy, C.J.3
Hibbs, D.E.4
Hursthouse, M.B.5
Morley, A.D.6
Sharp, B.W.7
Vicker, N.8
Warner, I.9
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14
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0029018955
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(c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
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(1995)
Tetrahedron
, vol.51
, pp. 6061
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Tanner, D.1
Almario, A.2
Högberg, T.3
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15
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0029018846
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(c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 3659
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Hong, H.1
Jagdmann, G.E.2
Hughes, P.F.3
Nichols, J.B.4
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16
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0011387836
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(c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
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(1996)
Synlett
, pp. 29
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Tuch, A.1
Albertini, E.2
Barco, A.3
Benetti, S.4
De Risi, C.5
Pollini, G.P.6
Zanirato, V.7
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17
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0030272833
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(c) Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans I 1995, 2355. For syntheses of the hexahydroazepine core, see: Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061.; Hong, H.; Jagdmann, G. E.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659; Tuch, A.; Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29; and Sanière, M.; Le Merrer, Y.; Depezay, J. Tetrahedron Asymm. 1996, 7, 2901.
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(1996)
Tetrahedron Asymm.
, vol.7
, pp. 2901
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Sanière, M.1
Le Merrer, Y.2
Depezay, J.3
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18
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0029798420
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(7) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Amer. Chem. Soc. 1996, 118, 10924.
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(1996)
J. Amer. Chem. Soc.
, vol.118
, pp. 10924
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Hansen, K.B.1
Leighton, J.L.2
Jacobsen, E.N.3
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20
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0000269981
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(9) The high regioselectivity of the nucleophilic attack is attributed to the preferred diaxial opening of conformationally constrained cyclohexene oxides. See Fürst, A.; Plattner, P. A. Helv. Chim. Acta 1949, 32, 275.
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(1949)
Helv. Chim. Acta
, vol.32
, pp. 275
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Fürst, A.1
Plattner, P.A.2
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21
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33845282179
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(10) Anelli, P. L., Biffi, C., Montanari, F., Quici, S. J. Org. Chem. 1987, 52, 2559.
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(1987)
J. Org. Chem.
, vol.52
, pp. 2559
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Anelli, P.L.1
Biffi, C.2
Montanari, F.3
Quici, S.4
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22
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0011477353
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The structure of 8 was confirmed by homonuclear decoupling experiments on the acetate ester
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(11) The structure of 8 was confirmed by homonuclear decoupling experiments on the acetate ester.
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23
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84910971057
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(12) Although no definitive stereochemical assignment was made, the major oxime is presumed to bear the sulfonate ester anti to the olefinic carbon; the observed isomeric product ratio is in line with results of previous studies on cyclohexenone oximes by Shoppee, C. W.; Akhtar, M. I.; Lack, R. E. J. Chem. Soc. 1964, 3392.
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(1964)
J. Chem. Soc.
, pp. 3392
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Shoppee, C.W.1
Akhtar, M.I.2
Lack, R.E.3
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