Multi-step reaction with 26 steps
1: 69 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 °C
2: 1.) dimethyl sulphide, N-chlorosuccinimide, 2.) triethylamine / 1.) toluene, ether, -20 deg C, 2 h, 2.) 30 min
3: 63 percent / benzene / 6 h / 80 °C
4: 86 percent / ethyl di-isopropylamine / CH2Cl2 / 2 h / Heating
5: 70 percent / Dowex 50W X-8 / methanol / 3 h / Ambient temperature
6: 95 percent / hydrogen / 10percent Pd-C / methanol / 4 h / 760 Torr
7: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min
8: 74 percent / butyl-lithium / hexane; tetrahydrofuran / 2 h / 0 °C
9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1M aq. NaOH, 30percent aq. hydrogen peroxide / 1.) THF, 4 h, reflux, 2.) 0 deg C, 30 min
10: 1.) dimethyl sulphoxide, oxalyl chloride, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 10 min, 2.) -60 deg C, 15 min, room temperature, 15 min
11: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) room temperature, 3 h
12: 98 percent / sodium hydroxide / methanol; H2O / 3 h / Ambient temperature
13: 95 percent / tetrahydrofuran / 12 h
14: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 7 h / -78 °C
15: 95 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 °C
16: m-chloroperoxybenzoic acid, 30percent aq. hydrogen peroxide / CDCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 15 min
17: 37 percent / toluene / 5 h / 100 °C
18: 98 percent / sodium hydroxide / H2O; methanol / 2 h / 0 °C
19: 65 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -20 deg C, 1 h, 2.) 0 deg C, 12 h
20: 51 percent / aluminium isopropoxide / o-xylene / 8 h / 125 °C
22: lithium di-isopropylamide
23: tetrabutylammonium fluoride
24: hydrogen peroxide, pyridine
25: NaBH4
26: pyridine
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; dimethylsulfide; Dowex 50W X-8; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; aluminum isopropoxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; chloroform-d1; hexane; dichloromethane; o-xylene; water; toluene; benzene;
