1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 93 percent Turnov. / sodium acetate / hexamethylphosphoric acid triamide / 24 h / 75 °C 4: 98 percent Turnov. / lithium aluminum hydride / diethyl ether / 0.17 h View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 85 percent / 18-crown-6 ether / acetonitrile / 288 h / Ambient temperature 4: 2.) hydrochloric acid / !:) ethyl ether, THF, reflux, 2.5 h, 2.) reflux, 3 h 5: 69 percent / ethanol / 2 h / Heating 6: 21 percent / tert-butyllithium / pentane; tetrahydrofuran / 1.) -78 deg C, 24 h, 2.) room temperature 7: 85 percent / m-chloroperbenzoic acid / CHCl3 / 24 h / 0 °C 8: 93 percent / boron trifluoride etherate / diethyl ether / 3 h / Ambient temperature View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 35 percent Turnov. / acetic acid / 39 h / 75 °C View Scheme

hydrogen; palladium on activated charcoal in methanol P=1034.3 Torr; 2 h;

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 1.) cuprous iodide / 1.) ethyl ether, 2.) 25 deg C, 30 h 4: 80 percent / 456 °C / 0.1 Torr View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 85 percent / acetic acid / 16 h / 75 °C View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 97 percent / xylene / 72 h / Heating 4: 1.) tert-butyllithium / 1.) pentane, 2.) reflux, 2 h 5: 550 °C / 0.1 Torr View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 85 percent / 18-crown-6 ether / acetonitrile / 288 h / Ambient temperature 4: 2.) hydrochloric acid / !:) ethyl ether, THF, reflux, 2.5 h, 2.) reflux, 3 h 5: 69 percent / ethanol / 2 h / Heating 6: 21 percent / tert-butyllithium / pentane; tetrahydrofuran / 1.) -78 deg C, 24 h, 2.) room temperature 7: 44 percent / 550 °C / 0.1 Torr View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 83 percent Turnov. / sodium methoxide / ethanol / 48 h / Heating 4: 93 percent / N-chlorosuccinimide / CCl4 / 12 h / Heating 5: 12 percent / aq sodium carbonate / 48 h / 20 - 25 °C / further reagents 6: 69 percent / Ambient temperature View Scheme

1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 97 percent / xylene / 72 h / Heating 4: 1.) tert-butyllithium / 1.) THF, 2.) reflux, 30 h 5: 95 percent / hydrogen bromide / CH2Cl2 / 1.) -78 deg C, 4 h, 2.) 25 deg C, 8 h View Scheme