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For prior consideration of the development of the C ring of lycorine by way of a Birch reduction. see: (a) Hendrickson, J. B.; Alder, R. W.; Dalton, D. R.; Hey, D. G. J. Org. Chem. 1969, 34, 2667. (b) Schultz, A. G. Acc. Chem. Res. 1990, 23, 207.
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16
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8944226491
-
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note
-
(b) Benzamide 3 is prepared by procedures described in ref 12a or may be purchased from Aldrich Chemical Co. (34,836-8).
-
-
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17
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-
8944244900
-
-
For the genesis of this procedure, see ref 12a
-
For the genesis of this procedure, see ref 12a.
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18
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8944228836
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Molecular modeling studies were carried out with MacroModel (MM2, Version 3.0)
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Molecular modeling studies were carried out with MacroModel (MM2, Version 3.0).
-
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22
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8944222940
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8944221086
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note
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Enamide 11c also was prepared via acylation of 9 with piperonyloyl chloride to give 10c.
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For an alternative mechanism involving intermolecular hydrogen atom migration, see (a) Schultz, A. G.; Lucci, R. D. J. Chem. Soc., Chem. Commun. 1976, 925. (b) Schultz, A. G.; Lucci, R. D.; Fu, W. Y.; Berger, M. H.; Erhardt, J.; Hagmann, W. K. J. Am. Chem. Soc. 1978, 100, 2150.
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CA 55:3594c
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CA 55:3594c.
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