Synthesis of Pentaprismane

Structure of Pentaprismane

C10H10

Principal investigatorPhilip E. Eaton
Publication year1981
Synthesis typeTotal
Number of steps 18 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Reflux, 48 h, 82%
intermediate structure
hv
Acetone
95%
intermediate structure
Li
NH3, t-BuOH, THF
-33 °C
intermediate structure
Pyr, TsCl
80% (2 steps)
intermediate structure
NaI
HMPA
110 °C, 48 h
intermediate structure + intermediate structure
t-BuLi
Et2O, Pentane
25 - 30 °C, , 50% (2 steps)
intermediate structure
hv
Acetone
intermediate structure
H2SO4
Et2O, H2O
RT, , 90% (2 steps)
intermediate structure
mCPBA
CH2Cl2
RT, , 90%
intermediate structure
KOH, NaIO4, RuO2
H2O
RT, ON, 80%
intermediate structure
CH2N2
CH2Cl2, Et2O
0 °C, , 95%
intermediate structure
Na
NH3
-33 °C, , 80%
intermediate structure
Me2S, Et3N, Cl2
CH2Cl2
intermediate structure
Pyr, TsCl
95 °C, 30 min, 80% (2 steps)
intermediate structure
KOH
H2O
110 °C, 5 h, 60 - 65%
intermediate structure
(COCl)2
Reflux
intermediate structure
Pyr, t-BuOOH
RT, ON
intermediate structure
2,4,6-triisopropylnitrobenzene
120 - 150 °C, , 42% (3 steps)
intermediate structure