Synthesis of Dodecahedrane

C20H20
Principal investigator | Leo A. Paquette |
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Publication year | 1982 |
Synthesis type | Total |
Number of steps | 26 (linear) |
References |
Part 1 of 1
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KOH
H2O, MeOH
Reflux, 60 min, 98%

NaHCO3,
KI3
H2O
RT, 23 h, 96%

NaOMe
MeOH
RT, 3 h, 96%


NH4Cl,
Zn-Cu
MeOH
RT, 5 h, 78%


KOH
DMSO
RT, 30 h, 77%
"The product depicted is the major component of an uncharacterized mixture of isomers."

H2O2,
NaOH
H2O, MeOH
RT, 2.5 h, 42%
See the Baeyer-Villiger Oxidation
"The product was selectively cristallized from the resulting mixture of isomers."

P2O5
MsOH
50 °C, 36.5 h, 83%

H2,
Pd/C
3 atm
EtOAc
100 °C, 16 h, 100%

NaBH3CN,
HCl
H2O, MeOH
RT, 8.5 h, 85%

HCl
MeOH
0 °C, 26 h, 62%

- Li
- BnOCH2Cl
NH3, THF
Reflux, 60 min, 48%


TsOH
PhH
70 °C, 8 h, 93%

H2O2,
NH2NH2
EtOH, H2O, THF
0 °C to RT, ON, 91%

i-Bu2AlH
PhH
RT, 12 h, 97%

HCrO3Cl.Pyr
CH2Cl2
RT, 90 min, 95%



HCrO3Cl.Pyr
CH2Cl2
RT, 4 h, 97%

KOH
EtOH, THF
RT, 5 h, 48%


TsOH
PhH
Reflux, 75 min, 100%

H2O2,
NH2NH2
EtOH, H2O, THF
0 °C to RT, ON, 91%

Pd/C
250 °C, 34%
