Synthesis of Cubane

Structure of Cubane

C8H8

Principal investigator	John Tsanaktsidis
Publication year	1997
Synthesis type	Total
Number of steps	10 (linear)
References	Aust. J. Chem. 1997, 50, 189. Synthesis 1995, 501.

Part 1 of 1

intermediate structure

(CH2OH)2, Dowex 50WX8

Dean-Stark

PhH

Reflux, 30 h, 90%

intermediate structure

Br2

Dioxane

RT, 2 d

intermediate structure

NaOH

MeOH

Reflux, 2 h, 60% (2 steps)

See the Diels-Alder Reaction

intermediate structure

H2SO4

RT, 30.5 h, 92%

intermediate structure

HCl

hν

H2O, MeOH

RT

intermediate structure

NaOH

H2O

Reflux, 5 h

See the Favorskii Rearrangement

intermediate structure

Dowex 50WX8

MeOH

Reflux, 24 h, 47% (3 steps)

See the Fischer-Speier Esterification

intermediate structure

NaOH

H2O, MeOH

Reflux, 4 h, 99%

intermediate structure

SOCl2

Reflux, 2 h

intermediate structure

Special reagent

DMAP, t-BuSH

hν

THF

Reflux, 90 min, 77% (2 steps)

See the Barton Decarboxylation

intermediate structure

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