Multi-step reaction with 8 steps
1: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 to -25 deg C, 2.5 h
2: p-TsOH*H2O / benzene / 1.5 h / Heating
3: 1.) Br2, 2.) DBU / 1.) CCl4, 25 deg C, 2 h, 2.) benzene, 25 deg C, 12 h
4: 82 percent / Pd(PPh3)4 / benzene / 15 h / Heating
5: 67 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / 17 h
6: aq. NaIO4 / diethyl ether / 1.25 h / 25 °C
7: glacial AcOH / 1.5 h / 25 - 90 °C
8: K2CO3 / 2.75 h / 25 °C
With
sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); bromine; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide;
In
diethyl ether; water; acetone; benzene;
DOI:10.1021/ja973715j