Synthesis of Corannulene

Structure of Corannulene

C20H10

Principal investigatorJay S. Siegel
Publication year1999
Synthesis typeTotal
Number of steps 10 (linear)
References
J. Am. Chem. Soc. 1999, 121, 7804. Tetrahedron Lett. 1993, 34, 273.
Part 1 of 1
intermediate structure
(CH2O)n, HCl
AcOH, H2O
50 °C, 24 h, 62%
See the Blanc Halomethylation
intermediate structure
KCN
Acetone, H2O
Reflux, 12 h, 99%
intermediate structure
H2SO4
AcOH, H2O
Reflux, 6 h, 90%
intermediate structure
SOCl2
CHCl3
Reflux, 60 min
intermediate structure
AlCl3
PhNO2
RT, 2 d, 82% (2 steps)
See the Friedel-Crafts Acylation
intermediate structure
SeO2
Dioxane , H2O
60 °C, 2 d, 91%
intermediate structure + intermediate structure
KOH
MeOH
RT, 30 min, 85%
See the Aldol Addition
See the Aldol Condensation
intermediate structure + intermediate structure
Ac2O
125 °C, 30 h, 74%
See the Diels-Alder Reaction
intermediate structure
NBS, Bz2O2
hν
CCl4
Reflux, 15 h, 100%
See the Wohl-Ziegler Reaction
intermediate structure
TiCl4, Zn-Cu
DME
Reflux, 2 d, 80%
intermediate structure
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