Narcissus and Daffodil

326 V.N. Bulavka and O.N. Tolkachev
R'
R'
HO
O
O
N
O
130 (R'=H, R''=Me)
131 (R'=R''=Me)
132 (R'=Ph, R''=Et )
133 (R'=Ph, R''=Bu)
HO
MeO
MeO
SiR''3
CF3
N
SiMe3
O
CF3
R'
R'
O
R'
R'
ylsilanyl)oxy-cyclohexanone and 2-bromo-3-hydroxy-4-methoxybenzaldehyde (54)
with a 2.7% total yield. Ishizaki et al. (1993), in a ten-step synthesis from guajacol
and benzoquinone ethylene monoketal, obtained a 11.3% total yield. The recently
published synthesis of Essamkaoui et al. (1996) contained only six steps, starting
from allylcyclohexenylveratrol.
O
O
O
SiR''3
134 (R'=H, R''=Me)
135 (R'=R''=Me)
136 (R'=Ph, R''=Et )
137 (R'=Ph, R''=Bu)
O
O
138 (R '=Ph )
139 (R '=Me )
140 141
O
N
N
O
O
CF3 CF3
Figure 12.16 Oxidative cyclisation reactions of trimethylsilanyl-substituted norbelladine-type
trifluoroacetamides to benzazepine spirodienones (Kita et al.,
1998).
MeO
MeO
N
CF3
O
CF3