Narcissus and Daffodil

Ph
Ph
O OH
O
O OMe
O OMe
Synthesis of galanthamine 323
OH
OH
O
O
Ph Ph
O
O
Ph Ph
OH
OH
109 110 111 112
Br
HO
O
OH
O
Ph Ph
N
Me3Si O
Ph
O
Ph
O
Me3Si
HO
O
of 124 with L-Selectride in tetrahydrofuran at –78 °C with following hydrolysis
gave 125, which on methylation with formaldehyde and formic acid gave sanguinine
(126) in 68% yield.
OH
O
Ph Ph
NH
Me3Si
Me3Si O
Ph
O
Ph
HO
113 114 115
O
SiMe3
N
O HO
CF3
O
O
N
O
CF3
HO
O
O
O
Ph Ph
N
O
CF3
Me3Si O
Ph
O
Ph
116 117 118
MeO
119 120 121
Figure 12.14 Synthesis of N,O-didemethyl-N-trifluoroacetylnarwedine (120) and N-demethyl-
N-trifluoroacetyl-narwedine (121) (Kita et al., 1998).
O
O
N
O
CF3