Synthesis of Fuchsiaefoline

Structure of Fuchsiaefoline

C24H31ClN2O3

Principal investigatorJames M. Cook
Publication year2004
Synthesis typeTotal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
K2CO3, LiCl, Pd(OAc)2
DMF
100 °C, , 75%
intermediate structure
  1. MeI
  2. NaH
DMF
intermediate structure
HCl
H2O, THF
0 °C to RT, , 90% (2 steps)
intermediate structure
Na2SO4, NaBH4, PhCHO
EtOH
-5 to 0 °C, ON, 90%
intermediate structure + intermediate structure
AcOH, CH2Cl2
0 °C to RT, ON
intermediate structure
CF3CO2H
CH2Cl2
RT, 7 d, 92% (2 steps)
intermediate structure
NaOMe
PhMe
Reflux, , 33%
intermediate structure
KOH
Dioxane
Reflux, , 80%
intermediate structure
H2, HCl, Pd/C
EtOH
RT, 7 h, 92%
intermediate structure + intermediate structure
K2CO3
THF
Reflux, 24 h, 90%
intermediate structure
K2CO3, Pd(OAc)2, Ph3P, n-Bu4N+ Br-
DMF, H2O
65 °C, 12 h, 80%
intermediate structure
KOt-Bu, Ph3P+CH2OMe Cl-
PhH
RT, 24 h
See the Wittig Reaction
intermediate structure
HCl
H2O, THF
55 °C, 6 h, 90% (2 steps)
intermediate structure
I2, KOH
EtOH
85%
intermediate structure
MeI
THF
0 °C
intermediate structure
AgCl
EtOH
RT, , 81% (2 steps)
intermediate structure