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(d) suomilide: K. Fujii, K. Sivonen, K. Adachi, K. Noguchi, Y. Shimizu, H. Sano, K. Hirayama, M. Suzuki, and K. Harada, Tetrahedron Lett., 1997, 38, 5529.
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(b) J. Quirante, C. Escolano, A. Merino, and J. Bonjoch, J. Org. Chem., 1998, 63, 968
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9
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0000627957
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For a recent approach to the morphan nucleus by formation of C(5)-C(6) bond involving a radical cyclization, see: G. A. Molander and C. H. Harris, J. Org. Chem., 1997, 62, 7418.
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H. Nagashima, N. Ozaki, M. Ishii, K. Seki, M. Washiyama, and K. Itoh, J. Org. Chem., 1993, 58, 464
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For the use of a dichloroacetamide as a proradical in this field, see: T. Sato, S. Ishida, H. Ishibashi, and M. Ikeda, J. Chem. Soc., Perkins Trans. 1, 1991, 353.
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0345442232
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The morphan stereoparent (10) had been synthesized starting from m-nitrophenylacetic acid derivatives by means of hydrogenation, followed by lactamization and further reduction of the resulting lactam: (a) M. W. Cronyn, J. Org. Chem., 1949, 14, 1013.
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0002639377
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Trichloroacetamide (7) was also available by trichloroacetylation (80%) of W-benzyl-N-(3-cyclohexenyl)amine, previously described by us: J. Quirante, C. Escolano, and J. Bonjoch, Synlett, 1997, 179.
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0345011160
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note
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3: C, 48.81; H, 4.64; N, 3.79; Cl, 38.42. Found: C, 49.08; H, 4.66; N, 3.81; Cl, 38.42.
-
-
-
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22
-
-
0344148673
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note
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3), 123.5 and 127.1 (C-1 and C-2), 161.1 (CO)
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-
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23
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84989052512
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For NMR data of 2-azabicicylo[3.3.1]nonane derivatives, see : (a) N. Casamitjana, J. Bonjoch, J. Gràcia, and J. Bosch, Magn. Reson. Chem., 1992, 30, 183.
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(b) J. Bonjoch, N. Casamitjana, J. Quirante, A. Torrens, A. Paniello, and J. Bosch, Tetrahedron, 1987, 43, 377.
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0345011159
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For the conformational preference of the nonbonding electron pair in NH piperidine derivatives, see: (a) J. B. Lambert, D. S. Bailey, and B. F. Michel, J. Am. Chem. Soc., 1972, 94, 3812.
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