Synthesis of [5.5.5.5]-Fenestratetraene

Structure of [5.5.5.5]-Fenestratetraene

C13H12

Principal investigatorJames M. Cook
Publication year1986
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure
SOCl2
Reflux, , 85%
intermediate structure
CH2N2
Et2O
87%
intermediate structure
PPh3
Et2O
93%
intermediate structure
NaNO2, HCl
H2O, THF
0 °C, , 80%
intermediate structure
Special reagent
NaHCO3
H2O, MeOH
RT, 12 h, 92%
intermediate structure
HCl, AcOH
H2O
87 °C, , 90%
intermediate structure
OsO4, NMO
Acetone, H2O
92%
intermediate structure
H2SO4, CrO3
Acetone, H2O
70%
See the Jones Oxidation
intermediate structure
Naphthalenesulfonic Acid
Cumene, Diglyme
Reflux, 4 d, 78%
intermediate structure
BH3.THF
THF
0 °C to RT, 50 h, 93%
intermediate structure
HMPA
Reflux, 48 h, 49%
intermediate structure