Multi-step reaction with 10 steps
1.1: montmorillonite K-10 / benzene / 20 - 40 °C
2.1: NaH / dimethylformamide / 10 h / 0 - 20 °C
3.1: 85 percent / PPh3 / 0.33 h / 0 °C
4.1: 91 percent / nBuLi / tetrahydrofuran / -78 - 20 °C
5.1: Red-Al / diethyl ether / 0.83 h / -78 - -10 °C
5.2: ethyl acetate / 0.25 h / -10 °C
5.3: I2 / tetrahydrofuran / 1 h / -78 - 0 °C
6.1: imidazole / dimethylformamide / 1.5 h / 0 - 20 °C
7.1: tBuLi / diethyl ether / 0.33 h / -78 °C
7.2: tetrahydrofuran / 0.42 h / -78 °C
7.3: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C
8.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
9.1: SmI2 / tetrahydrofuran / 0.03 h / 0 °C
With
1H-imidazole; n-butyllithium; samarium diiodide; oxalyl dichloride; montmorillonite K-10; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
9.1: Swern oxidation;
DOI:10.1002/anie.200453801