Synthesis of [6.5]Coronane

C24H36

Principal investigator	Lutz Fitjer
Publication year	1987
Synthesis type	Total
Number of steps	9 (linear)
References	Angew. Chem. Int. Ed. Engl. 1987, 26, 130. Tetrahedron Letters 1983, 24, 5351. Chem. Ber. 1988, 121, 525. J. Org. Chem. 1966, 31, 480. Chem. Ber. 1988, 121, 2171.

Part 1 of 1

Et3N

Et2O, PhH

50 °C, 25 h, 70%

NaOMe

PhMe

Reflux, 1 h, 68%

KOt-Bu

PhH

Reflux, 24.5 h, 50%

See the Wittig Reaction

																																							mCPBA
																																				
																																							BF3.OEt2
																																				
																	CH2Cl2															

								RT, 								80 min, 								71%
							
								See the Semi-Pinacol Rearrangement
							
								"62:38 Trans:Cis"

NH2NH2.H2O, KOH

Triethylene glycol

140 to 190 °C, 6 h, 40-49%

See the Wolff-Kishner Reduction

AllylMgBr

																	Et2O															

								Reflux, 								6 h, 								60%
							
								See the Grignard Reaction
							
								"Also isolated was the equatorial alcohol (stable conformer, 17% yield)"

SOCl2

Pyr

0 °C to RT, 9 h, 92%

Cp2ZrHCl
NBS

PhH

RT, 3 h, 82%

AIBN, n-Bu3SnH

PhH

80 °C, 63 h, 8%

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