1: p-TsOH / acetone 2: H2 / Pd black / methanol 3: borane, dimethylsulfide / tetrahydrofuran 4: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 5: NaH / tetrahydrofuran; dimethylformamide 6: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 7: mesyl chloride, triethylamine / CH2Cl2 View Scheme

Multi-step reaction with 4 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide  

Multi-step reaction with 9 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: N,N-diethylaniline5: 10 percent HCl / methanol / 40 °C6: NaH / tetrahydrofuran; dimethylformamide7: 10 percent HCl / methanol / 70 °C8: 2.) copper(I) iodide / 2.) THF, dimethylsulfide9: NaH / tetrahydrofuran; dimethylformamide  

Multi-step reaction with 8 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: N,N-diethylaniline5: 10 percent HCl / methanol / 40 °C6: NaH / tetrahydrofuran; dimethylformamide7: 10 percent HCl / methanol / 70 °C8: 2.) copper(I) iodide / 2.) THF, dimethylsulfide  

Multi-step reaction with 10 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: N,N-diethylaniline5: 10 percent HCl / methanol / 40 °C6: NaH / tetrahydrofuran; dimethylformamide7: 10 percent HCl / methanol / 70 °C8: 2.) copper(I) iodide / 2.) THF, dimethylsulfide9: NaH / tetrahydrofuran; dimethylformamide10: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF  

Multi-step reaction with 11 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: N,N-diethylaniline5: 10 percent HCl / methanol / 40 °C6: NaH / tetrahydrofuran; dimethylformamide7: 10 percent HCl / methanol / 70 °C8: 2.) copper(I) iodide / 2.) THF, dimethylsulfide9: NaH / tetrahydrofuran; dimethylformamide10: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF11: mesyl chloride, triethylamine / CH2Cl2