Multi-step reaction with 14 steps
1.1: 89 percent / Raney Nickel; H2 / ethanol / 3 h / 20 °C / 760 Torr
2.1: 90 percent / imidazole / CH2Cl2 / 16 h / 20 °C
3.1: 87 percent / isopropylmagnesium chloride / tetrahydrofuran / -30 - 0 °C
4.1: 93 percent / MgBr2*Et2O; n-tributyltin chloride / CH2Cl2 / 5 h / 20 °C
5.1: 89 percent / tetrahydrofuran / 2 h / 0 °C
6.1: EtBOMe; NaBH4 / tetrahydrofuran; methanol / 9 h / -78 °C
6.2: H2O2 / methanol; tetrahydrofuran; H2O / -78 - 20 °C
7.1: 3.80 g / PPTs / CH2Cl2 / 1 h / 20 °C
8.1: 86 percent / pyridine; O3; Sudan III / Ph3P / CH2Cl2; methanol / -78 - 20 °C
9.1: n-Bu2BOTf; Et3N / CH2Cl2 / 1.5 h / -78 - 0 °C
9.2: 93 percent / CH2Cl2 / 2 h / -78 - 0 °C
10.1: 73 percent / AlMe3 / tetrahydrofuran / 10 h / -10 - 0 °C
11.1: 82 percent / 2,6-lutidine / CH2Cl2 / 3 h / -78 °C
12.1: 88 percent / DIBAL-H / CH2Cl2; toluene / 3 h / -78 °C
13.1: chlorodicycloheylborane; Et3N / diethyl ether / 1.67 h / -78 - 0 °C
13.2: diethyl ether / 21 h / -78 - -20 °C
13.3: 40 percent / H2O2 / diethyl ether; methanol; H2O / 1 h / 0 °C / pH 7
14.1: 70 percent / Zn(BH4)2 / CH2Cl2; diethyl ether / 4 h / 0 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; zinc(II) tetrahydroborate; oil scarlet; di-n-butylboryl trifluoromethanesulfonate; dicyclohexylboron chloride; tributyltin chloride; hydrogen; trimethylaluminum; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; nickel; diisobutylaluminium hydride; ozone; triethylamine; magnesium bromide;
triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/ol051225n