Multi-step reaction with 9 steps
1: 1.) DCC, DMSO 2.) pyridinium trifluoroacetate / 1.) benzene, room t., 2.) benzene, 70 deg C, 20 min
2: DBU / CHCl3 / 1 h / Ambient temperature
3: CH(OMe)3 / p-Tos-OH / 48 h / Ambient temperature
4: 1.) 0.5 M 9-BBN(THF) 2.) 3 M aq. NaOH, 30percent H2O2 / 1.) THF, 0 deg C to room t., 90 min, 2.) THF, 0 deg C, 15 min
5: 76 percent / PCC, NaOAc / CH2Cl2 / 2 h / 23 °C
6: 1.) BuLi(hexane) / 1.) DMSO, with cooling, then 10 min, 23 deg C, 2.) DMSO, 23 deg C
7: 50percent aq. HCl / CHCl3; propan-2-ol / 0.5 h
8: 1.) NaH / 1.) THF, 23 deg C, 1 h 2.) THF, 0 deg C, then 45 deg C, 3 h
9: 7.6 mg / NaBH4 / ethanol / -20 °C
With
hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; 9-BBN-THF; dihydrogen peroxide; sodium acetate; pyridinium trifluroacetate; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; pyridinium chlorochromate; trimethyl orthoformate;
toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
ethanol; dichloromethane; chloroform; isopropyl alcohol;
DOI:10.1016/0223-5234(88)90209-7