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(c) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Williard, P. G. J. Am. Chem. Soc. 1998, 120, 7429.
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(a) Meyers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc 1985, 107, 7776.
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(h) Hughes, R. C.; Dvorak, C. A.; Meyers, A. I. J. Org. Chem. 2001, 66, 5545.
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See also, i
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See also, (i) Schwarz, J. B.; Meyers, A. I. J. Org. Chem. 1998, 63, 1619.
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Amat, M.; Escolano, C.; Lozano, O.; Gómez-Esqué, A.; Griera, R.; Molins, E.; Bosch, J. J. Org. Chem. 2006, 71, 3804.
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Bosch, J.7
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Soteras, I.; Lozano, O.; Gómez-Esqué A.; Escolano, C.; Orozco, M.; Amat, M.; Bosch, J.; Luque, F. J. J. Am. Chem. Soc. 2006, 128, 6581.
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20
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34250204040
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The absolute configuration of the dialkylated lactams 9a and 10a was unambiguously confirmed by X-ray crystallographic analysis.
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The absolute configuration of the dialkylated lactams 9a and 10a was unambiguously confirmed by X-ray crystallographic analysis.
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21
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0035215106
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For the synthesis of enantioenriched (ee = 42%) lactam 15 by asymmetric dialkylation of a chiral N-(dialkylamino)lactam, see: Enders, D.; Teschner, P.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 2001, 4463.
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For the synthesis of enantioenriched (ee = 42%) lactam 15 by asymmetric dialkylation of a chiral N-(dialkylamino)lactam, see: Enders, D.; Teschner, P.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 2001, 4463.
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(a) Ziegler, F. E.; Kloek, J. A.; Zoretic, P. A. J. Am. Chem. Soc. 1969, 91, 2342.
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(c) Imanishi, T.; Miyashita, K.; Nakai, A.; Inoue, M.; Hanaoka, M. Chem. Pharm. Bull 1983, 31, 1191.
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Szántay, C.; Bölcskei, H.; Gács-Baitz, E.; Keve, T. Tetrahedron 1990, 46, 1687.
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0024338679
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(-)-Quebrachamine was also obtained, although in poorer yield (5%), when the reduction was carried out with BH3 in THF at reflux, following the conditions reported for the complete reduction of related seven-membered keto lactams: Khandelwal, Y.; Jain, P. C.; Anand, N. Indian J. Chem. B 1989, 28B, 475.
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(-)-Quebrachamine was also obtained, although in poorer yield (5%), when the reduction was carried out with BH3 in THF at reflux, following the conditions reported for the complete reduction of related seven-membered keto lactams: Khandelwal, Y.; Jain, P. C.; Anand, N. Indian J. Chem. B 1989, 28B, 475.
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(a) Takano, S.; Sato, M.; Hatakeyama, S.; Hirama, M.; Ogasawara, K. Heterocycles 1976, 5, 221.
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(b) Takano, S.; Hatakeyama, S.; Ogasawara, K. J. Am. Chem. Soc. 1979, 101, 6414.
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4 reduction of related tetracyclic nine-membered 16-oxolactams, see: (a) Narisada, M.; Watanabe, F.; Nagata, W. Tetrahedron Lett. 1971, 39, 3681.
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4 reduction of related tetracyclic nine-membered 16-oxolactams, see: (a) Narisada, M.; Watanabe, F.; Nagata, W. Tetrahedron Lett. 1971, 39, 3681.
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Ziegler, F. E.; Bennett, G. B. J. Am. Chem. Soc. 1973, 95, 7458. See also ref 5.
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(b) Ziegler, F. E.; Bennett, G. B. J. Am. Chem. Soc. 1973, 95, 7458. See also ref 5.
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(a) Kutney, J. P.; Abdurahman, N.; Gletsos, C.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc 1970, 92, 1727.
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37049096415
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For previous enantioselective syntheses of the alkaloids, and, )-quebrachamine, see: a
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For previous enantioselective syntheses of the alkaloids (+)- and (-)-quebrachamine, see: (a) Takano, S.; Chiba, K.; Yonaga, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1980, 616.
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(c) Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628.
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Fujimura, T.; Nakashima, H.; Sakagami, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2002, 43, 97. See also refs 15c, d, e.
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(d) Fujimura, T.; Nakashima, H.; Sakagami, H.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2002, 43, 97. See also refs 15c, d, e.
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