Multi-step reaction with 11 steps
1.1: 2,6-lutidine / CH2Cl2 / 14 h / 20 °C
2.1: p-toluenesulfonic acid hydrate / methanol; CH2Cl2 / 19.5 h / 20 °C
3.1: NaH / dimethylformamide / 0.25 h / 20 °C
3.2: 35.53 g / dimethylformamide / 16 h / 20 °C
4.1: 5.53 g / aq. OsO4; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C
5.1: NaIO4 / tetrahydrofuran; H2O / 9 h / 20 °C
6.1: 5.24 g / MgBr2*Et2O / CH2Cl2 / 2 h / -78 - 20 °C
7.1: NaH / dimethylformamide / 0.5 h / 20 °C
7.2: 100 percent / dimethylformamide / 4.5 h / 0 °C
8.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H2O / 9 h / 20 °C
9.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
10.1: 1.33 g / Sc(OTf)3 / benzene / 20 °C
11.1: 70 percent / CH2Cl2; hexane / 2 h / 20 °C
With
2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; magnesium bromide; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo010974p