Multi-step reaction with 13 steps
1.1: tBuOK; TBAI / tetrahydrofuran / 0.5 h / 23 °C
2.1: ethanedithiol; BF3Et2O / CH2Cl2 / 0.5 h / -20 °C
3.1: 93 percent / PPTS / benzene / 12 h / Heating
4.1: 85 percent / LiAlH4; AlCl3 / CH2Cl2; diethyl ether / 2 h / 23 °C
5.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -20 °C
6.1: NHMDS / tetrahydrofuran / 0.25 h / -20 °C
7.1: LDA / tetrahydrofuran / 0.25 h / -20 °C
7.2: 98 percent / tetrahydrofuran / 0.5 h / -78 °C
8.1: 69 percent / PTS / methanol / 0.5 h / 23 °C
9.1: 73 percent / TMSOTf; Et3SiH / CH2Cl2 / 0.5 h / 0 °C
10.1: 87 percent / imidazole / dimethylformamide / 0.5 h / 23 °C
11.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.17 h / -78 °C
12.1: DDQ / CH2Cl2 / 0.17 h / 23 °C / pH 7
13.1: TMSOTf; Et3SiH / CH2Cl2 / 0.5 h / 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; triethylsilane; ethandithiol; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/j.tetlet.2005.09.164