Multi-step reaction with 12 steps
1: 95 percent / sodium iodide / acetone / 36 h / Ambient temperature
2: 1.) lithium diisopropylamide, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (DMPU) / 1.) THF, -78 deg C, 45 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 18 h
3: 1.) lithium diisopropylamide / 1.) hexane, THF, -78 deg C, 45 min, 2.) hexane, THF, -78 deg C, 1 h
4: 1.) ozone, 2.) PPh3 / 1.) CH2Cl2, -78 deg C, 10 min, 2.) CH2Cl2, RT, 5 h
5: 86 percent / BF3*OEt2 / CH2Cl2 / 0.17 h / -78 °C
6: 90 percent / 10-camphorsulfonic acid / benzene / Heating
7: 1.) potassium hexamethyldisilazide / 1.) THF, toluene, -78 deg C, 40 min, 2.) THF, toluene, -78 deg C, 1 h
8: 97 percent / silver perchlorate / benzene; H2O
9: 90 percent / NaIO4, NaHCO3 / methanol; tetrahydrofuran; H2O / 5 h
10: 99 percent / sodium borohydride / methanol / -20 °C
11: 100 percent / triethylamine / CH2Cl2 / 0.42 h / -10 °C
12: 100 percent / LiBr / tetrahydrofuran / 0.25 h
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; silver perchlorate; potassium hexamethylsilazane; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; sodium iodide; lithium bromide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;