Synthesis of Pentaprismane

Structure of Pentaprismane

C10H10

Principal investigator	Philip E. Eaton
Publication year	1981
Synthesis type	Total
Number of steps	18 (linear)
References	J. Am. Chem. Soc. 1981, 103, 2134.

Part 1 of 1

intermediate structure

+

intermediate structure

Reflux, 48 h, 82%

See the Diels-Alder Reaction

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

See the Finkelstein Reaction

intermediate structure

+

intermediate structure

t-BuLi

Et2O, Pentane

25 - 30 °C, 50% (2 steps)

See the Grob Fragmentation

intermediate structure

hv

Acetone

intermediate structure

H2SO4

Et2O, H2O

RT, 90% (2 steps)

intermediate structure

mCPBA

CH2Cl2

RT, 90%

See the Baeyer-Villiger Oxidation

intermediate structure

KOH, NaIO4, RuO2

H2O

RT, ON, 80%

intermediate structure

CH2N2

CH2Cl2, Et2O

0 °C, 95%

intermediate structure

Na

NH3

-33 °C, 80%

See the Pinacol Coupling

intermediate structure

Me2S, Et3N, Cl2

CH2Cl2

See the Corey-Kim Oxidation

intermediate structure

Pyr, TsCl

95 °C, 30 min, 80% (2 steps)

intermediate structure

KOH

H2O

110 °C, 5 h, 60 - 65%

See the Favorskii Rearrangement

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

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