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2005
Alkaloids
U 0600
06- 183
1-Methylgalanthamine Derivatives. — For structure—activity-relationships studies
1-methylgalanthamine derivatives are prepared. 1-Methylnarwedine (IX) is synthesized in a sequence analogous to the industrial synthesis of (-)-galanthamine from
benzaldehyde derivative (I). An X-ray crystallographic analysis of racemic (IX) reveals
the impossibility of a crystallization-induced asymmetric transformation to enantiopure
(IX). Stereoselective reduction of (IX) yields 1-methylgalanthamine. Its epi-derivatives
(X) is a key intermediate for the synthesis of further 6-epi-derivatives like (XI) and
(XIII). Derivatives of 1-methylgalanthamine are prepared similarly. —
(HEMETSBERGER, M.; TREU, M.; JORDIS, U.; MEREITER, K.; HAMETNER, C.;
FROEHLICH*, J.; Monatsh. Chem. 135 (2004) 10, 1275-1287; Inst. Appl. Synth.
Chem., Tech. Univ., A-1060 Wien, Austria; Eng.) — H. Hoennerscheid
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