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Orjales, A.6
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5
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20444464610
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11
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0029880916
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For a related homoallylic radical rearrangement of a tropane derivative leading to a 6-azabicyclo[3.2.1]octane, see: Rigby, J. H.; Pigge, F. C. Tetrahedron Lett. 1996, 37, 2201-2204.
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Pigge, F.C.2
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12
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33748647052
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For a related desymmetrization of a carbamate-protected (saturated) tropinone, see: Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc., Perkin Trans. 1 1997, 1307-1313.
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J. Chem. Soc., Perkin Trans. 1
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Momose, T.1
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Eugster, C.H.5
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16
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20444493348
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CDCC 265105 available at http://www.ccdc.cam.ac.uk.
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17
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33748651908
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Momose, T.; Toshima, M.; Seki, S.; Koike, Y.; Toyooka, N.; Hirai, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1315-1321.
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Toyooka, N.5
Hirai, Y.6
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18
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20444473928
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note
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Careful control of the temperature is necessary to avoid competitive removal of the bromine substituent, followed by further reduction. Very slow warming up of the cooling bath must be performed with a critical stage around -15°C where most of the reduction occurs.
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19
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20444490930
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CDCC 265106 available at http://www.ccdc.cam.ac.uk.
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21
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0023907210
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Krow, G. R.; Shaw, D. A.; Lynch, B.; Lester, W.; Szczepanski, S. W.; Raghavachari, R.; Derome, A. E. J. Org. Chem. 1988, 53, 2258-2262.
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Krow, G.R.1
Shaw, D.A.2
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Raghavachari, R.6
Derome, A.E.7
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22
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0000141607
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Kuwajima, I.; Nakamura, E.; Shimizu, M. J. Am. Chem. Soc. 1982, 104, 1025-1030.
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Kuwajima, I.1
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25
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20444435676
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See Supporting Information
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See Supporting Information.
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26
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20444504908
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CDCC 265107 available at http://www.cdcc.cam.ac.uk.
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27
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20444480374
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CDCC 265108 available at http://www.ccdc.cam.ac.uk.
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28
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20444448652
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note
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In light of our results, Prof. Krow reassessed the NMR experiments originally used to assign 12 and 7-epi-12 in ref 17 and agrees that the C-7 stereochemical assignments should be reversed.
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29
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85004247144
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Synthesis of 1 would require ≃10 further steps from 12. See also: Imanishi, T.; Yagi, N.; Hanaoka, M. Chem. Pharm. Bull. 1985, 33, 4202-4211.
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Imanishi, T.1
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30
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33947092471
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Trost, B. M.; Godleski, S. A.; Genêt, J. P. J. Am. Chem. Soc. 1978, 100, 3930-3931.
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Trost, B.M.1
Godleski, S.A.2
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31
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0021062003
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Kunng, F.-A.; Gu, J.-M.; Chao, S.; Chen, Y.; Mariano, P. S. J. Org. Chem. 1983, 48, 4262-4266.
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Mariano, P.S.5
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34
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0000174970
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Ethyl epimer of 1 has also been previously prepared using Trost's cyclization procedure, in 20% yield, see: Tomisawa, H.; Hongo, H.; Kato, H.: Sato, K.; Fujita, R. Heterocycles 1981, 16, 1947-1950.
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Fujita, R.5
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