Synthesis of Dodecahedrane

C20H20

Principal investigator	Leo A. Paquette
Publication year	1982
Synthesis type	Total
Number of steps	26 (linear)
References	J. Am. Chem. Soc. 1974, 96, 4671. J. Org. Chem. 1979, 44, 3616. J. Am. Chem. Soc. 1981, 103, 228. J. Am. Chem. Soc. 1982, 104, 4502. J. Am. Chem. Soc. 1982, 104, 4503. J. Am. Chem. Soc. 1983, 105, 5446.

Part 1 of 1

THF

-78 °C to RT, 23%

See the Diels-Alder Reaction

KOH

H2O, MeOH

Reflux, 60 min, 98%

NaHCO3, KI3

H2O

RT, 23 h, 96%

NaOMe

MeOH

RT, 3 h, 96%

CrO3, H2SO4

Acetone, H2O

5 °C, 2.5 h, 92%

See the Jones Oxidation

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."