Multi-step reaction with 25 steps
1: 91 percent / 4-DMAP, Et3N / CH2Cl2 / 1 h / 0 °C
2: 81 percent / BF3*Et2O, TMSOTf / acetonitrile / 3 h / 0 °C
3: 100 percent / MeONa / methanol / 24 h / 25 °C
4: 1.) n-Bu2SnO, 2.) CsF / 1.) MeOH, reflux, 4 h, 2.) DMF, 40 deg C, 16 h
5: 1.) imidazole, NaH
6: 60 percent / n-Bu3SnH, AIBN / toluene / 1 h / 110 °C
7: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -78 deg C, 20 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT, 7 h
8: 83 percent / Ph3P, I2, imidazole / CH2Cl2 / 2 h / 40 °C
9: 1.) LDA / 1.) Et2O, hexane, 0 deg C, 4 h, 2.) Et2O, hexane, from -110 deg C to RT, 12 h
10: 97 percent / O3 / CH2Cl2 / -78 °C
11: 1.) TiCl4, Et3N / 1.) CH2Cl2, -78 deg C, 2.5 h, 2.) CH2Cl2, -78 deg C, 2.5 h
12: 89 percent / SmI2 / tetrahydrofuran / 1 h / -10 °C
13: 86 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 - 20 °C
14: 99 percent / H2 / 10percent Pd/C / ethanol / 48 h / Ambient temperature
15: Et3N, SOCl2 / CH2Cl2 / 0.17 h / 0 °C
16: RuCl3, NaIO4 / CCl4; acetonitrile; H2O / 1.5 h / 0 °C
17: 1.) t-BuLi, HMPA, 3.) 30percent aq. H2SO4
18: 91 percent / NBS, AgClO4 / acetone; H2O / 0.01 h / 0 °C
19: 1.) n-Bu3B, air, 2.) NaBH4, 3.) 30percent aq. H2O2, 2.5M aq. NaOH
20: 93 percent / CSA / CH2Cl2 / 3 h / 0 °C
21: 97 percent / Dibal-H / CH2Cl2; toluene / 4 h / -78 °C
22: 85 percent / HF*pyridine / CH2Cl2 / 1.5 h / 0 °C
23: 95 percent / MnO2 / CH2Cl2 / 4 h / Ambient temperature
24: 1.) BuLi / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, hexane, from 0 deg C to RT, 18 h
25: 91.5 percent / aq. NaOH / methanol; tetrahydrofuran / 6 h / Ambient temperature
With
1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; manganese(IV) oxide; ruthenium trichloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; n-butyllithium; thionyl chloride; samarium diiodide; air; 2,2'-azobis(isobutyronitrile); tributyl borane; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium methylate; silver perchlorate; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; pyridine hydrogenfluoride; ozone; triethylamine; triphenylphosphine; cesium fluoride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; acetone; toluene; acetonitrile;