1: Jone's reagent / acetone / 0 - 4 °C 2: sulfuric acid / 20 °C 3: hydrogen; ethylenediamine / ethanol; water View Scheme

1: Jone's reagent / acetone / 0 - 4 °C 2: sulfuric acid / 20 °C 3: hydrogen; ethylenediamine / ethanol; water View Scheme

1: anhydrous 1-octyne With n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=-60°C; 0.5 h; 2: 1-bromo-10-[tetrahydropyranyloxy]decane in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=-20 - 20°C;

1: p-TSA 2: n-BuLi View Scheme

1: 88.7 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 2: 1.) diborane, 2.) PCC, sodium acetate / 1) THF, 0 deg C (2 h), RT (2 h); 2) CH2Cl2, reflux, 4 h 3: 78.8 percent / CH2Cl2 / 26 h 4: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 5: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h View Scheme

1: 95.4 percent / LAH / diethyl ether / 2 h 2: 88.7 percent / PPTS / CH2Cl2 / 4 h / Ambient temperature 3: 1.) diborane, 2.) PCC, sodium acetate / 1) THF, 0 deg C (2 h), RT (2 h); 2) CH2Cl2, reflux, 4 h 4: 78.8 percent / CH2Cl2 / 26 h 5: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 6: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h View Scheme

1: 78.8 percent / CH2Cl2 / 26 h 2: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 3: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h View Scheme

1: 1.) diborane, 2.) PCC, sodium acetate / 1) THF, 0 deg C (2 h), RT (2 h); 2) CH2Cl2, reflux, 4 h 2: 78.8 percent / CH2Cl2 / 26 h 3: 47 percent / Li-Hg / diethyl ether / 20 h / Ambient temperature 4: 1.) n-BuLi / 1) THF; 2) HMPT, THF, below 25 deg C, 0.5 h View Scheme

1: lithium amide / liquid ammonia / 2 h 2: 1.) lithium amide / 1.) NH3 (liquid), 2.) NH3(liquid), THF 3: 70 percent / sodium amide, 1,3-diaminopropane / 80 °C 4: 95.8 percent / PTSA / CH2Cl2 / Ambient temperature 5: 1.) lithium amide / 1.) NH3 (liquid), THF, 3 h, 2.) 1 h View Scheme

1: 1.) lithium amide / 1.) NH3 (liquid), 2.) NH3(liquid), THF 2: 70 percent / sodium amide, 1,3-diaminopropane / 80 °C 3: 95.8 percent / PTSA / CH2Cl2 / Ambient temperature 4: 1.) lithium amide / 1.) NH3 (liquid), THF, 3 h, 2.) 1 h View Scheme