Multi-step reaction with 11 steps
1.1: 96 percent / mCPBA; NaHCO3 / CH2Cl2 / 12 h / 20 °C
2.1: 100 percent / camphorsulfonic acid / 16 h / Heating
3.1: 84 percent / camphorsulfonic acid / CH2Cl2 / 36 h
4.1: 65 percent / lithium aluminum hydride / diethyl ether / 5 h / 0 - 20 °C
5.1: 80 percent / pyridinium p-toluenesulfonic acid / CH2Cl2 / 19 h
6.1: o-nitrophenylselenocyanate; tri-n-butylphosphine / tetrahydrofuran / 1 h / 0 °C
6.2: 71 percent / aq. H2O2 / tetrahydrofuran / 3 h / 0 - 45 °C
7.1: 82 percent / pyridinium p-toluenesulfonic acid / methanol / 2 h
8.1: 69 percent / DDQ / CH2Cl2 / 0.5 h / 20 °C
9.1: N,N-dimethylaminopyridine; dicyclohexylacarbodiimide / CH2Cl2 / 1.5 h / 0 - 20 °C
10.1: 78 percent / tetrakis(triphenylphosphine)palladium; LiCl; cuprous chloride / dimethylsulfoxide / 18 h / 20 - 60 °C
11.1: 82 percent / diisopropylethylamine / diethyl ether / 3 h / Heating
With
dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; lithium chloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja060847g