Total synthesis of (-)-balanol

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4397-4407

  Miyabe, Hideto ^a   Torieda, Mayumi ^a   Inoue, Kyoko ^a   Tajiri, Kazumi ^a   Kiguchi, Toshiko ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BALANOL; PROTEIN KINASE C INHIBITOR;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PSEUDOMONAS;

EID: 0032568895     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980208r     Document Type: Article

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27. For other preparations of the hexahydroazepine-containing fragment, see the following. (a) Recently, total syntheses of balanol were also achieved by Tanner's group. See: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, L; Cösregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857-4868. (b) Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061-6070. (c) Müller, A.; Takyar, D. K.; Witt, S.; König, W. Liebigs Ann. Chem. 1993, 651- 655. (d) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29-30. (e) Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2909. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
28. For other preparations of the hexahydroazepine-containing fragment, see the following. (a) Recently, total syntheses of balanol were also achieved by Tanner's group. See: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, L; Cösregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857-4868. (b) Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061-6070. (c) Müller, A.; Takyar, D. K.; Witt, S.; König, W. Liebigs Ann. Chem. 1993, 651- 655. (d) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29-30. (e) Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2909. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
29. For other preparations of the hexahydroazepine-containing fragment, see the following. (a) Recently, total syntheses of balanol were also achieved by Tanner's group. See: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, L; Cösregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857-4868. (b) Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061-6070. (c) Müller, A.; Takyar, D. K.; Witt, S.; König, W. Liebigs Ann. Chem. 1993, 651- 655. (d) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29-30. (e) Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2909. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
30. For other preparations of the hexahydroazepine-containing fragment, see the following. (a) Recently, total syntheses of balanol were also achieved by Tanner's group. See: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, L; Cösregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857-4868. (b) Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061-6070. (c) Müller, A.; Takyar, D. K.; Witt, S.; König, W. Liebigs Ann. Chem. 1993, 651- 655. (d) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29-30. (e) Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2909. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
31. For other preparations of the hexahydroazepine-containing fragment, see the following. (a) Recently, total syntheses of balanol were also achieved by Tanner's group. See: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, L; Cösregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857-4868. (b) Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061-6070. (c) Müller, A.; Takyar, D. K.; Witt, S.; König, W. Liebigs Ann. Chem. 1993, 651- 655. (d) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29-30. (e) Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2909. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
32. For other preparations of the hexahydroazepine-containing fragment, see the following. (a) Recently, total syntheses of balanol were also achieved by Tanner's group. See: Tanner, D.; Tedenborg, L.; Almario, A.; Pettersson, L; Cösregh, I.; Kelly, N. M.; Andersson, P. G.; Högberg, T. Tetrahedron 1997, 53, 4857-4868. (b) Tanner, D.; Almario, A.; Högberg, T. Tetrahedron 1995, 51, 6061-6070. (c) Müller, A.; Takyar, D. K.; Witt, S.; König, W. Liebigs Ann. Chem. 1993, 651- 655. (d) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29-30. (e) Tuch, A.; Sanière, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2909. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
33. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
34. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
35. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
36. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
37. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
38. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
39. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
40. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
41. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
42. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
43. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
44. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
45. For some recent studies on balanol analogues, see: (a) Lai, Y.- S.; Mendoza, J. S.; Jagdmann, G. E., Jr.; Menaldino, D. S.; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226-235. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E., Jr.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215-5227. (c) Lai, Y.-S.; Stamper, M. Bioorg. Med. Chem. Lett. 1995, 5, 2147-2150. (d) Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E., Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151-2154. (e) Lai, Y.-S.; Mendoza, J. S.; Hubbard, F.; Kalter, K. Bioorg. Med. Chem. Lett. 1995, 5, 2155-2160. (f) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216. (g) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Bioorg. Med. Chem. Lett. 1996, 6, 973-978. (h) Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 1759- 1764. (i) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799-5802. (j) Crane, H. M.; Menaldino, D. S.; Jagdmann, G. E., Jr.; Darges, J. W.; Buben, J. A. Bioorg. Med. Chem. Lett. 1995, 5, 2133- 2138. (k) Heerding, J. M.; Lampe, J. W.; Darges, J. W.; Stamper, M. L. Bioorg. Med. Chem. Lett. 1995, 5, 1839-1842. Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2015-2020. (m) Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chem. Biol. 1995, 2, 601-608.
46. For our total synthesis of (-)-balanol, see: (a) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580-582. (b) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626.
47. For our total synthesis of (-)-balanol, see: (a) Miyabe, H.; Torieda, M.; Kiguchi, T.; Naito, T. Synlett 1997, 580-582. (b) Naito, T.; Torieda, M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. Chem. Pharm. Bull. 1996, 44, 624-626.
48. For recent reviews, see: (a) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-194. (b) Snider, B. B. Chem. Rev. 1996, 96, 339-364. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301-856.
49. For recent reviews, see: (a) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-194. (b) Snider, B. B. Chem. Rev. 1996, 96, 339-364. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301-856.
50. For recent reviews, see: (a) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-194. (b) Snider, B. B. Chem. Rev. 1996, 96, 339-364. (c) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 301-856.
51. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Translated by Lomas, J.; John Wiley & Sons Inc.: New York, 1995; pp 151-158, 243-255.
52. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
53. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
54. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
55. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
56. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
57. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
58. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
59. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
60. We reported the first example of the synthesis of five- to seven- membered cyclic amino alcohols in the tributyltin hydride-induced radical cyclization of oxime ethers. See: (a) Naito, T.; Tajiri, K. Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205-2206. (b) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253-256. O-Stannyl ketyl radical cyclization of alkenes, see: (c) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939-4942. A few outstanding examples of the radical-mediated formation of seven-membered ring were reported. For recent examples, see: (d) Giese, B.; Kopping, B.; Göbel. T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. (N.Y.) 1996, 48, 315-317. (e) Gibson, S. E.; Guillo, N.; Tozer, M. J. Chem. Commun. 1997, 637-638. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662. (g) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051-9052. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943- 944. (i) Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031-4034.
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65. For our recent work in radical addition to oxime ethers, see: (a) Miyabe, H.; Ushiro, G.; Naito, T. Chem. Commun. 1997, 1789- 1790. (b) Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631-634.
66. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
67. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
68. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
69. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
70. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
71. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
72. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
73. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
74. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
75. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
76. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365- 1368. (j) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888. (k) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3932. Della, E. W.; Knill, A. M. Aust. J. Chem. 1994, 47, 1833-1841.
77. For selected examples of the radical reaction of oxime ethers, see: (a) Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186-8199. (b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138-5139. (c) Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631-1633. (d) Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549-550. (e) Marco- Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202-1209. (f) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (g) Hollingworth, G. J.; Pattenden, G.; Schulz, D. J. Aust. J. Chem. 1995, 48, 381-399. (h) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010-6011. (i)
78. Bartlett, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 110, 1633-1634.
79. For reviews, see: (a) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
80. For reviews, see: (a) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345-347. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
81. 2, see: (a) Marco-Contelles, J.; Gallego, P.; Rodríguez-Fernández, M.; Khiar, N.; Destabel, C.; Bernabé, M.; Martínez-Grau, A.; Chiara, J. L. J. Org. Chem. 1997, 62, 7397- 7412. (b) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555- 3556.
82. 2, see: (a) Marco-Contelles, J.; Gallego, P.; Rodríguez-Fernández, M.; Khiar, N.; Destabel, C.; Bernabé, M.; Martínez-Grau, A.; Chiara, J. L. J. Org. Chem. 1997, 62, 7397- 7412. (b) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555- 3556.
83. 2 was reported, the N-O bond cleavage of 8b could not be observed. See: (a) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (b) Chiara, J. L.; Destabel, C.; Gallego, P.; Marco-Contelles, J. J. Org. Chem. 1996, 61, 359-360.
84. 2 was reported, the N-O bond cleavage of 8b could not be observed. See: (a) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366-8367. (b) Chiara, J. L.; Destabel, C.; Gallego, P.; Marco-Contelles, J. J. Org. Chem. 1996, 61, 359-360.
85. 2, the chelated intermediates were proposed. See: (a) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265- 1276. (b) Taniguchi, N.; Uemura, M. Synlett 1997, 51-53. (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. (d) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373-376.
86. 2, the chelated intermediates were proposed. See: (a) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265- 1276. (b) Taniguchi, N.; Uemura, M. Synlett 1997, 51-53. (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. (d) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373-376.
87. 2, the chelated intermediates were proposed. See: (a) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265- 1276. (b) Taniguchi, N.; Uemura, M. Synlett 1997, 51-53. (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. (d) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373-376.
88. 2, the chelated intermediates were proposed. See: (a) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265- 1276. (b) Taniguchi, N.; Uemura, M. Synlett 1997, 51-53. (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. (d) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373-376.
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95. (b) Hydroxyanthraquinones 15ab could be directly converted into the corresponding methylated anthracene derivatives 17ab by treatment with sodium hydrosulfite in the presence of tetrabutylammonium bromide as a PTC followed by methylation employing dimethyl sulfate and KOH. See: Kraus, G. A.; Man, T. O. Synth. Commun. 1986, 16, 1037-1042.
96. The reason trimethoxy-substituted benzophenone 20 was obtained from 17b even in the absence of methanol and/or other methylating agents is not clear at the moment.
97. 6 330.1102, found 330.1115.
98. Yield in parentheses is based on the consumed starting material.
99. Mukaiyama T. Angew. Chem., Int. Ed. Engl. 1979, 18, 707-721