Narcissus and Daffodil

PhCH2O
MeO
MeO
MeO
PhCH2O
O
101
MeO
104
MeO
PhCH2O
MeO
Br
NMe
Br
O
OMe
O
NMe
OMe
N
Br
105 (R=H)
106 ( )
R=CF 3
R''O
R'O
MeO
R
O
MeO
RO
MeO
NMe
Br
Synthesis of galanthamine 321
unreacted starting materials. Yields were dependent on the character of substitution
in the substrate molecules. In the case of benzyloxy-substituted compounds,
yields of the expected compounds reached 25–40%.
The incomplete transformation of amides 96–98 and 102 to the key compounds
99–100 and 103 was explained by the existence of starting compounds as a
O
96 (R'=R''=Me)
97 ( R'=R''=PhCH2 )
98 ( R'=PhCH2, R''=Me)
O
NMe
Br
MeO
R'O
MeO
RO
O
Br
99 (R'=Me)
100 ( R'=PhCH2)
O
Br
NMe
+ 34
O
O
+ 49
NMe
102 103
R=Me, PhCH2
R=Me, PhCH2
PhCH2O
MeO
MeO
OMe
N
OMe
Br
107 (R=H)
108 ( R=CF3)
Figure 12.13 Synthesis of narwedine-type enones and dienones by electrochemical oxidation
of belladine-type amides (Vlahov et al., 1980a,b, 1984).
R
O