Multi-step reaction with 13 steps
1.1: 90 percent / CSA / dimethylformamide / 38 °C
2.1: SO3*pyridine; i-Pr2NEt / dimethylsulfoxide / 1 h / 20 °C
3.1: NaHMDS / 0 - 20 °C
3.2: 4 h / 0 °C
4.1: CSA; H2O / methanol; CH2Cl2 / 7 h / 40 °C
5.1: imidazole; DMAP / dimethylformamide; CH2Cl2 / 12 h / 20 °C
6.1: 38 percent / CSA / 48 h / 40 °C
7.1: TBAF / tetrahydrofuran / 1.5 h
8.1: pyridine / CH2Cl2 / 0 - 20 °C
9.1: 98 percent / DMP; pyridine / CH2Cl2
10.1: t-BuLi; MgBr2*Et2O / benzene / 25 h / -78 - 20 °C
10.2: 70 percent / MgBr2*Et2O / CH2Cl2; benzene / 0.75 h / 0 °C
11.1: 81 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
12.1: 88 percent / super-hydride / tetrahydrofuran / 0.58 h / 0 °C
13.1: 98 percent / DMP / pyridine / 1.5 h / 20 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; pyridine-SO3 complex; phthalic acid dimethyl ester; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sodium hexamethyldisilazane; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; magnesium bromide;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
3.1: Wittig reaction / 9.1: Dess-Martin oxidation;
DOI:10.1021/ol0262284