Multi-step reaction with 14 steps
1.1: 90 percent / TsOH*H2O / methanol / 0.33 h / 25 °C
2.1: 99 percent / (COCl)2; Et3N; DMSO / CH2Cl2 / 1 h / -78 - 25 °C
3.1: 99 percent / MgBr2 / diethyl ether / 3 h / 0 °C
4.1: 95 percent / imidazole; 4-DMAP / CH2Cl2 / 16 h / 20 °C
5.1: BH3*SMe2 / tetrahydrofuran / 7 h / 0 - 25 °C
5.2: 85 percent / aq. NaOH; H2O2 / tetrahydrofuran; diethyl ether / 16 h / 0 - 25 °C
6.1: 93 percent / (COCl)2; Et3N; DMSO / CH2Cl2 / 1 h / -78 - 25 °C
7.1: diethyl ether; tetrahydrofuran / 3 h / -78 °C
7.2: 62.3 g / aq. NaOH; H2O2 / tetrahydrofuran; diethyl ether / 16 h / 0 - 25 °C
8.1: 89 percent / imidazole; 4-DMAP / CH2Cl2 / 7 h / 20 °C
9.1: O3 / CH2Cl2 / -78 °C
9.2: 92 percent / PPh3 / CH2Cl2 / 1 h / -78 - 25 °C
10.1: diethyl ether; tetrahydrofuran / 3 h / -78 °C
10.2: 59.79 g / aq. NaOH; H2O2 / tetrahydrofuran; diethyl ether / 16 h / 0 - 25 °C
11.1: 95 percent / imidazole; 4-DMAP / CH2Cl2 / 7 h / 20 °C
12.1: O3 / CH2Cl2 / -78 °C
12.2: 90 percent / PPh3 / CH2Cl2 / 1 h / -78 - 25 °C
13.1: 98 percent / NaBH4 / methanol / 0.17 h / 0 °C
14.1: 98 percent / PPh3; I2; imidazole / benzene / 0.5 h / 0 - 25 °C
With
1H-imidazole; dmap; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide borane complex; iodine; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; magnesium bromide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
2.1: Swern oxidation / 6.1: Swern oxidation / 7.1: Brown allylation / 10.1: Brown allylation;
DOI:10.1039/b602020h