Multi-step reaction with 20 steps
1: 86 percent / n-BuLi / tetrahydrofuran / 3 h / -78 - 0 °C
2: 50 percent / H2 / Pd/C / ethyl acetate / 7 h
3: Ca/liq.NH3 / diethyl ether / 1 h / -78 °C
4: IBX / dimethylsulfoxide / 20 h / Ambient temperature
5: NaBH4 / methanol / 3 h / 0 °C
6: NaH / tetrahydrofuran / Ambient temperature
7: H2SO4 / acetic acid; H2O / 12 h / Ambient temperature
8: NaIO4 / methanol; H2O / 3 h / Ambient temperature
9: NaH / tetrahydrofuran / 5 h / -78 °C
10: K2CO3 / methanol / 1 h / Ambient temperature
11: DIBAL-H / toluene / 0.5 h / -78 °C
12: CSA / 2 h / 0 °C
13: 98 percent / H2 / Rh-Al2O3 / diethyl ether / 0.17 h / 0 - 5 °C
14: H2SO4 / acetic acid; H2O / 10 h / Ambient temperature
15: 78 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 0 °C
16: NaH / tetrahydrofuran / 3 h / Ambient temperature
17: 9-BBN, NaOH, H2O2 / tetrahydrofuran / 5 h / Ambient temperature
18: (COCl)2, DMSO, Et3N / CH2Cl2 / 0.75 h / -78 °C
19: Zn dust, aq. NH4Cl / tetrahydrofuran / 12 h / Ambient temperature
20: 85 percent / NaH / tetrahydrofuran / Ambient temperature
With
sodium hydroxide; sodium tetrahydroborate; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; ammonia; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; calcium; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
palladium on activated charcoal; rhodium on alumina;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1016/S0040-4039(98)00588-7