Synthesis of [5.5.5.5]-Fenestratetraene

Structure of [5.5.5.5]-Fenestratetraene

C13H12

Principal investigator	James M. Cook
Publication year	1986
Synthesis type	Total
Number of steps	11 (linear)
References	J. Am. Chem. Soc. 1985, 107, 4786. Tetrahedron 1986, 42, 1597. Tetrahedron 1981, 37, 4521.

Part 1 of 1

intermediate structure

SOCl2

Reflux, 85%

intermediate structure

CH2N2

Et2O

87%

intermediate structure

PPh3

Et2O

93%

intermediate structure

NaNO2, HCl

H2O, THF

0 °C, 80%

intermediate structure

Special reagent

NaHCO3

H2O, MeOH

RT, 12 h, 92%

See the Weiss-Cook Condensation

intermediate structure

HCl, AcOH

H2O

87 °C, 90%

intermediate structure

OsO4, NMO

Acetone, H2O

92%

See the Upjohn Dihydroxylation

intermediate structure

H2SO4, CrO3

Acetone, H2O

70%

See the Jones Oxidation

intermediate structure

Naphthalenesulfonic Acid

Cumene, Diglyme

Reflux, 4 d, 78%

intermediate structure

BH3.THF

THF

0 °C to RT, 50 h, 93%

intermediate structure

HMPA

Reflux, 48 h, 49%

intermediate structure

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