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For the preparation and biological evaluation of balanol analogues see the following for leading references: (a) 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. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; 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. (c) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E.; 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. (d) Mendoza, J. S.; Jagdmann, G. E.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211 and references therein.
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For the preparation and biological evaluation of balanol analogues see the following for leading references: (a) 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. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; 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. (c) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E.; 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. (d) Mendoza, J. S.; Jagdmann, G. E.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211 and references therein.
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For the preparation and biological evaluation of balanol analogues see the following for leading references: (a) 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. (b) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; 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. (c) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E.; 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. (d) Mendoza, J. S.; Jagdmann, G. E.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211 and references therein.
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For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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For further syntheses of the hexahydroazepine segment see: (a) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615. (b) Morie, T.; Kato, S. Heterocycles 1998, 48, 427. (c) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177. (d) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651. (e) Tuch, A.; Sanière, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymm. 1996, 7, 2901. (f) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693.
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note
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(a) The synthesis described by Naito et al. requires nine steps and includes the resolution of racemic 3 as the final steps, cf. ref 7. (b) Very recently, an RCM-based approach to 3 has been reported that is distictly different from our one; it makes use of D-serine as the starting material and comprises a 14-step linear sequence, cf. ref 12a.
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For a short account see: Fürstner, A. Synlett 1999, 1523.
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33750595439
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3 as shown in Scheme 4. Originally, it was believed that the complex thus formed is a ruthenium allenylidene species: cf. Harlow, K. J.; Hill, A. F.; Winton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. More detailed study, however, has shown that it is the rearranged product, i.e., the indenylidene ruthenium complex 18: cf. Hill, A. F.; Fürstner, A.; Liebl, M.; Mynott, R.; Gabor, B.; Jafarpour, L.; Nolan, S. P., manuscript in preparation.
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33750595439
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manuscript in preparation
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3 as shown in Scheme 4. Originally, it was believed that the complex thus formed is a ruthenium allenylidene species: cf. Harlow, K. J.; Hill, A. F.; Winton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285. More detailed study, however, has shown that it is the rearranged product, i.e., the indenylidene ruthenium complex 18: cf. Hill, A. F.; Fürstner, A.; Liebl, M.; Mynott, R.; Gabor, B.; Jafarpour, L.; Nolan, S. P., manuscript in preparation.
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