Multi-step reaction with 13 steps
1: 29 percent / 9-BBN / 3 h / Heating
2: imidazole / dimethylformamide / 1 h / Ambient temperature
3: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
4: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
5: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
6: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
7: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
8: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
9: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
10: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
11: DCC, DMAP / CH2Cl2; dimethylformamide / 1 h / Ambient temperature
12: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / Ambient temperature
13: CH2Cl2 / 0.25 h / Ambient temperature
With
pyridine; 1H-imidazole; peracetic acid; dmap; sodium hydroxide; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; jones' reagent; trifluorormethanesulfonic acid; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; acetic acid; benzenesulfonyl chloride; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a804275f