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15444381098
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note
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73% yield of 5 was due to the highly acid-sensitive nature of 5.
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19
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0021173291
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For the installation of a quaternary carbon center in the Birch reduction, see for examples: (a) Schultz, A. G.; Sundararaman, P. Tetrahedron Lett. 1984, 25, 4591. (b) Donohoe, T. J.; Guyo, P. M. J. Org. Chem. 1996, 61, 7664.
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Sundararaman, P.2
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For the installation of a quaternary carbon center in the Birch reduction, see for examples: (a) Schultz, A. G.; Sundararaman, P. Tetrahedron Lett. 1984, 25, 4591. (b) Donohoe, T. J.; Guyo, P. M. J. Org. Chem. 1996, 61, 7664.
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Donohoe, T.J.1
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+ thereby enhancing the nucleophilicity of the enolate; see for an example: Donohoe, T. J.; Guyo, P. M.; Harji, R. R.; Helliwell, M. Tetrahedron Lett. 1998, 39, 3075.
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0033550480
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For synthesis and biological activities of lamellarin I, see: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54. For that of lamellarins K and L, see ref 5.
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For the suppression of Birch over-reduction by converting benzoic acid to a carboxylate salt, see: Mander, L. N.; Morris, J. C. J. Org. Chem. 1997, 62, 7497.
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15444368482
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note
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Introduction of alkoxide had dramatically increased the energy of LUMO (3.55 eV in 22 vs -0.17 eV and -0.48 eV for 17 and 19, respectively), which resulted in significantly slower reduction (6 h for 22 vs 10-20 min for 17 and 19).
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25
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15444373166
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note
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For complications in Birch reduction in the presense of an internal proton source, see ref 14.
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26
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0034703322
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Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179.
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27
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15444377279
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note
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The relative configuration of 32 was confirmed by a NOESY experiment. NOE was observed between the hydrogen at C-4 and the methyl group at C-5 (so it was between the methyl group at the C-4 position and the hydrogen at the C-5 position).
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28
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0032499011
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(a) Dean, P. O.; George, R.; Kaye, P. T. Tetrahedron 1998, 54, 3871.
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