1: 9-(3-phenylpropyl)-9-borabicyclo[3.3.1]nonane With potassium tert-butylate in 1,4-dioxane; 2-methyl-propan-1-ol T=20°C; 0.5 h; 2: cyclopentyl-bromide With N,N'-dimethylcyclohexane-1,2-diamine; [NiCl2(1,2-dimethoxyethane)] in 1,4-dioxane; 2-methyl-propan-1-ol T=20°C; Suzuki cross-coupling; 24 h; Further stages.;

AgBr; potassium fluoride in diethyl ether; dichloromethane T=-10°C; 15 h; Inert atmosphere;

CuBr*Me2S-LiBr; lithium thiophenoxide; magnesium 1) THF, reflux, 2 h; 2) THF, HMPA, 67 deg C, 48 h; further reagents; Yield given. Multistep reaction;

CuBr*Me2S-LiBr; lithium thiophenoxide; magnesium 1) THF, reflux, 2 h; 2) THF, HMPA, 67 deg C, 48 h; Yield given. Multistep reaction;

1: diethyl ether 3: platinum; ethanol / Hydrogenation View Scheme

Hydrogenation;

T=300 - 310°C; Hydrogenation;