Multi-step reaction with 12 steps
1: 1.) Mg / 1.) ether, 2.) ether, 8 h, RT
2: 54 percent / I2 / CHCl3 / 2 h / Heating
3: 1.) O3, 2.) LiAlH4 / 1.) hexane, -45 deg C, 2.) hexane, ether, from -45 to -35 deg C
4: 94 percent / Br2, NaHCO3, HMPA / CH2Cl2 / 0 °C
5: 95 percent / TosOH*H2O / toluene / 2 h / Heating
6: 90 percent / pyridine / 40 h / 4 °C
7: 1.) NaN3, 2.) LiAlH4 / 1.) N-methyl-2-pyrrolidinone, 3 h, 100 deg C, 2.) ether, 3 h
8: 98 percent / 2 h / Heating
9: N2O4, NaHCO3 / diethyl ether / 1 h / 0 °C
10: 1.) t-BuOK, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 1 h, -30 deg C, 2.) THF, 16 h, RT
11: 1.) LDA / 1.) THF, 30 min, -78 deg C, 2.) THF, 30 min, -78 deg C
12: 1.) MsCl, Et3N, 2.) Et3N / 1.) toluene, 2 h, RT, 2.) toluene, 48 h, reflux
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; sodium azide; potassium tert-butylate; bromine; iodine; dinitrogen tetraoxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; magnesium; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide;
In
diethyl ether; dichloromethane; chloroform; toluene;