Multi-step reaction with 8 steps
1: 92 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 0.5 h / -50 °C
2: imidazole / dimethylformamide / 12 h / 25 °C
3: 1) O3, pyridine, Sudan IV, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) up to 25 deg C, 1 h
4: 16 percent / MgBr2 / CH2Cl2 / 50 h / 25 °C
5: 1) NaH / 1) DMF, 25 deg C
6: 1) O3, pyridine, Sudan IV, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) up to room temp., 1.5 h
7: 100 percent / LiAlH4 / diethyl ether / 0.33 h / -50 °C
8: 88 percent / DDQ, 3 Angstroem molecular sieves / CH2Cl2 / 0.33 h
With
pyridine; 1H-imidazole; 1-[{2-methyl-4-(2-methylphenylazo)-phenyl}-azo]-2-naphthalenol; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; sodium hydride; ozone; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)96139-3