Multi-step reaction with 20 steps
1: p-TsOH / benzene / 24 h / Heating
2: 80 percent / mCPBA / CH2Cl2 / 24 h / -20 - 0 °C
3: iPr2NEt / CH2Cl2 / 0.5 h / -78 °C
4: 1) mCPBA, KHCO3, 2) citric acid / 1) CH2Cl2, -30 to -20 deg C, 1 h, 2) MeOH, 0 deg C to RT
5: NaIO4 / methanol; H2O / 0 deg C, 12 h; RT, 3 h
6: CHCl3 / Ambient temperature
7: 71 percent / LTBA / tetrahydrofuran / -78 to -40 deg C; -35 deg C, 4 h
8: 89 percent / nBu3P / tetrahydrofuran / 1 h / 0 - 20 °C
9: 85 percent / 30percent H2O2 / tetrahydrofuran / 18 h / 0 - 20 °C
10: I2, NaHCO3 / CH2Cl2 / 48 h / Ambient temperature
11: 90 percent / methanol / 4 h / 0 - 20 °C
12: LTBA / tetrahydrofuran / 3 h / 0 °C
13: pyridine / 2 h / 0 - 20 °C
14: 56 percent / CSA, dihydroquinone / benzene / 3 h / Heating
15: 1) mCPBA, 2) 2N HCl / 1) CH2Cl2, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h
16: Me4NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C
17: DDQ / dioxane / 4 h / 80 °C
18: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature
19: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature
20: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C
With
pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium periodate; osmium(VIII) oxide; tributylphosphine; camphor-10-sulfonic acid; dihydrogen peroxide; iodine; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; citric acid; silver(l) oxide; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetic acid; acetonitrile; benzene;
DOI:10.1016/0040-4039(96)01332-9