Narcissus and Daffodil

MeO
MeO
MeO
HN
Me
O
O
O
O
OMe
O
Br
Me
N
HN
Me
S
O
Synthesis of galanthamine 315
HN
Me
and subsequent aminolysis produced (+)-carboxamide ((+)-75) (37%). The O-acetyl
derivative 76 (89%) was transformed into the cyano derivative 77 (POCl 3 ), and
LiAlH 4 reduction afforded benzazepine of the structure (+)-78 in 42% yield. The
OMe
OMe
O
OMe
62 63 64
HO
(–)-65
Br
O
NMe
O
MeO
Me Br
N
O
60
61
O
OMe
O
OMe
O
OMe
OH
O
O
NMe
MeO
O
Br
Br
(–)-34 (–)-66
Figure 12.9 (Above) 4-Methoxybenzyl-protected intermediates for the synthesis of galanthamine
(1) (Vlahov et al., 1978, 1989). (Below) Microbiological reduction of
bromo-narwedinone (34) (Vlahov et al., 1984).
NMe