1: 3-(phenylsulfonyl)cyclohex-1-ene With n-butyllithium in tetrahydrofuran T=-30°C; 1.5 h; 2: oxirane in tetrahydrofuran T=-30 - 20°C;

sodium ethanolate in ethanol T=180°C; 19 h; var. temp.; Title compound not separated from byproducts;

n-butyllithium; bis(trimethylsilyl)-peroxide 1.) THF, -78 deg C; 15 min; 2.) room temp.; Yield given. Multistep reaction;

1: 1.) n-BuLi / 1.) THF, -70 degC, 15 min 2.) 1 h 2: 73 percent / potassium tert-butoxide / 2-methyl-propan-2-ol / 6 h / 80 °C View Scheme

palladium 10 on activated carbon; hydrogen in methanol T=20°C; P=760.051 Torr; 24 h;

palladium diacetate; n-butyllithium; lithium triethylborohydride 1.) THF, -78 deg C, 1 h; room temperature, 2 h, 2.) room temperature, 30 min, 3.) THF, 0 deg C, 2 h; room temperature, 20 h; Yield givenMultistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

palladium diacetate; n-butyllithium; lithium triethylborohydride 1.) THF, -78 deg C, 1 h; room temperature, 2 h, 2.) room temperature, 30 min, 3.) THF, 0 deg C, 2 h; room temperature, 20 h; Yield givenMultistep reaction. Yields of byproduct given. Title compound not separated from byproducts;