Synthesis of Dodecahedrane

Structure of Dodecahedrane

C20H20

Part 1 of 1
intermediate structure + intermediate structure
THF
-78 °C to RT, , 23%
intermediate structure
KOH
MeOH, H2O
Reflux, 60 min, 98%
intermediate structure
KI3, NaHCO3
H2O
RT, 23 h, 96%
intermediate structure
NaOMe
MeOH
RT, 3 h, 96%
intermediate structure
CrO3, H2SO4
Acetone, H2O
5 °C, 2.5 h, 92%
See the Jones Oxidation
intermediate structure
Zn-Cu, NH4Cl
MeOH
RT, 5 h, 78%
intermediate structure + intermediate structure
KOH
DMSO
RT, 30 h, 77%
"The product depicted is the major component of an uncharacterized mixture of isomers."
intermediate structure
H2O2, NaOH
MeOH, H2O
RT, 2.5 h, 42%
"The product was selectively cristallized from the resulting mixture of isomers."
intermediate structure
P2O5
MsOH
50 °C, 36.5 h, 83%
intermediate structure
H2, Pd/C
EtOAc
100 °C, 16 h, 100%
intermediate structure
NaBH3CN, HCl
MeOH, H2O
RT, 8.5 h, 85%
intermediate structure
HCl
MeOH
0 °C, 26 h, 62%
intermediate structure
  1. Li
  2. BnOCH2Cl
NH3, THF
Reflux, 60 min, 48%
intermediate structure
Et3N
PhH, t-BuOH
RT, 18 h, 90%
intermediate structure
TsOH
PhH
70 °C, 8 h, 93%
intermediate structure
NH2NH2, H2O2
THF, EtOH, H2O
0 °C to RT, ON, 91%
intermediate structure
i-Bu2AlH
PhH
RT, 12 h, 97%
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 90 min, 95%
intermediate structure
PhMe, MeOH
-78 °C to RT, 18 h, 36%
intermediate structure
Li
NH3, THF, EtOH
Reflux, 60 min, 90%
See the Birch Reduction
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 4 h, 97%
intermediate structure
KOH
THF, EtOH
RT, 5 h, 48%
intermediate structure
Et3N
PhH, t-BuOH
RT, 10 h, 100%
intermediate structure
TsOH
PhH
Reflux, 75 min, 100%
intermediate structure
NH2NH2, H2O2
THF, EtOH, H2O
0 °C to RT, ON, 91%
intermediate structure
Pd/C
250 °C, , 34%
intermediate structure