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For articles on septicine and synthetic analogues, see: a) V. M. Sharma, K. V. A. Seshu, C. V. Krishna, P. Prasanna, V. C. Sekhar, A. Venkateswarlu, S. Rajagopal, R. Ajaykumar, D. S. Deevi, N. V. S. Rao-Mamidi, R. Rajagopalan, Bioorg. Med. Chem. Lett. 2003, 13, 1679-1682;
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23944484268
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note
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2,3 = 8.0, 9.1 Hz. It must be taken into account that free rotation around the C2-C2′ bond is possible, and hence the experimental constants may not completely match those calculated for the minimum-energy conformations.
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62
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20444483055
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Theoretical coupling constants were calculated over the minimised structures (MMFF force field) for all possible isomers, by using the Karplus-Altona equation implemented in the Macromodel 7.0 program. See: C. A. G. Haasnoot, F. A. A. M. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783-2792.
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23944456149
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note
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13C NMR spectrum of the mixture resembles that of compound 19, and shows olefinic (C) signals corresponding either to another diastereomer or to double-bond position isomers. The estimated 81% yield was calculated from the weight of the mixture isolated after column chromatography.
-
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64
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23944499360
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note
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10b,1 = 5.1, 11.6 Hz for the (10aR*,10bR*) diastereomer.
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65
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