Multi-step reaction with 11 steps
1.1: MgSO4 / methanol; H2O / 12 h / 20 °C
2.1: imidazole / dimethylformamide / 10 h / 20 °C
3.1: DIBAL / CH2Cl2; toluene / 1 h / -78 °C
4.1: 12.30 g / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 0 °C
5.1: carbonyl diimidazole / tetrahydrofuran / 3 h / 20 °C
5.2: tetrahydrofuran / 24 h / 20 °C
6.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C
6.2: tetrahydrofuran; various solvent(s) / 12 h / 20 °C
7.1: 13.14 g / DIBAL / toluene; tetrahydrofuran / 2 h / -78 °C
8.1: 57 percent / Pd(OAc)2; PPh3; Et3N / dimethylformamide / 6 h / 30 °C
9.1: 2,6-lutidine; LiCl / dimethylformamide / 0.5 h / 0 °C
9.2: 81 percent / methanesulfonyl chloride / dimethylformamide / 2 h / 0 °C
10.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -50 °C
11.1: 1.07 g / aq. H2O2 / CHCl3 / 0.02 h
With
1H-imidazole; 2,6-dimethylpyridine; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium chloride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
8.1: Mizoroki-Heck reaction;
DOI:10.1021/ja003976k