Multi-step reaction with 11 steps
1: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
2: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating
3: 1) butyllithium, diisopropylamine / 1) hexane, THF,-70 deg C, 30 min, 2) THF, 15 min
4: 1) ozone, 2) pyridine / 1) CH2Cl2, -74 deg C, 2 h, 2) -74 deg C up to room temp.
5: 65 percent / OsO4, N-methylmorpholine N-oxide / H2O; acetone; 2-methyl-propan-2-ol / 15 h / Ambient temperature
6: 98 percent / PPTS / acetone / 10 h / Ambient temperature
7: 95 percent / methanol / 0.5 h / Heating
8: 95 percent / 18-crown-6, tri-n-butyl phosphine, CCl4 / acetonitrile / 1a) 30-40 deg C, 1 h, 1b) 70-80 deg C, 2 h
9: 92 percent / DMAP / acetonitrile / 1 h / Ambient temperature
10: 70 percent / LiOH*H2O / tetrahydrofuran; H2O / 0.5 h / Ambient temperature
11: 70 percent / DEPC, Et3N / dimethylformamide / 1a) 0 deg C, 3 h, 1b) room temp., 20 h
With
pyridine; tetrachloromethane; lithium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; tributylphosphine; 4 A molecular sieve; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; diethyl dicarbonate;
dmap;
In
tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)82406-6