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For comprehensive reviews on biological activities and synthetic studies of galanthamine-type Amaryllidaceae alkaloids, see:. Brossi A. (Ed), Academic Press, New York, NY
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For comprehensive reviews on biological activities and synthetic studies of galanthamine-type Amaryllidaceae alkaloids, see:. Martin S.F. In: Brossi A. (Ed). The Alkaloids Vol. 30 (1987), Academic Press, New York, NY 251-376
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0035902882
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Recent reports on racemic syntheses of galanthamine, see:
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Recent reports on racemic syntheses of galanthamine, see:. Node M., Kodama S., Hamashima Y., Baba T., Hamamichi N., and Nishide K. Angew. Chem., Int. Ed. 40 (2001) 3060-3062
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16
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0141490558
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For chiral total syntheses of (+)- and (-)-galanthamine, see:
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For chiral total syntheses of (+)- and (-)-galanthamine, see:. Tomioka K., Shimizu K., Yamada S.-i., and Koga K. Heterocycles 6 (1977) 1752-1756
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Kodama S., Hamashima Y., Nishide K., and Node M. Angew. Chem., Int. Ed. 43 (2004) 2659-2661
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24
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0028024493
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For preparation of (-)-galanthamine via spontaneous resolution of racemic narwedine, see:
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For preparation of (-)-galanthamine via spontaneous resolution of racemic narwedine, see:. Shieh W.-C., and Carlson J.A. J. Org. Chem. 59 (1994) 5463-5465
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2, see:
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2, see:. Mulzer J., Bats J.W., List B., Opatz T., and Trauner D. Synlett (1997) 441-444
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Mulzer, J.1
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0000128663
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For utilization of Claisen rearragement in the synthesis of related alkaloids, see:
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For utilization of Claisen rearragement in the synthesis of related alkaloids, see:. Keck G.E., and Webb II R.R. J. Org. Chem. 47 (1982) 1302-1309
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Webb II, R.R.2
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Labidalle S., Min Z.Y., Reynet A., Moskowitz H., Vierfond J.-M., and Miocque M. Tetrahedron 44 (1988) 1159-1169
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0033065781
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see also Ref. 9
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Mulzer J., and Trauner D. Chirality 11 (1999) 475-482 see also Ref. 9
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Chirality
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Mulzer, J.1
Trauner, D.2
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41
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34547685756
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note
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13C NMR, IR, and mass spectrometric and/or elemental analyses.
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-
43
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0001685085
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Johnson W.S., Werthemann L., Bartlett W.R., Brocksom T.J., Li T.-T., Faulkner D.J., and Petersen M.R. J. Am. Chem. Soc. 92 (1970) 741-743
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Johnson, W.S.1
Werthemann, L.2
Bartlett, W.R.3
Brocksom, T.J.4
Li, T.-T.5
Faulkner, D.J.6
Petersen, M.R.7
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46
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34547659815
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-
note
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+, 287.1521.
-
-
-
-
47
-
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34547683198
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-
note
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When propionic acid was employed as the acid in the Johnson-Claisen rearrangement of 4, the yield of 3 was found to be low (less than 25%) and the formation of significant amount of unidentified by-products was observed.
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