Multi-step reaction with 12 steps
1.1: 66 percent / CsF / Pd(PPh3)4; CuI / dimethylformamide / 24 h / 45 °C
2.1: 43 percent / AD-mix α / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C
3.1: 95 percent / imidazole / dimethylformamide / 1 h / 20 °C
4.1: BH3*THF / tetrahydrofuran / 27 h / 0 - 20 °C
4.2: 73 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0 - 20 °C
5.1: 92 percent / imidazole / dimethylformamide / 24 h / 20 °C
6.1: 73 percent / MeOH; 10-camphorsulfonic acid / CH2Cl2 / 5 h / 0 °C
7.1: 99 percent / SO3*pyridine; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C
8.1: 90 percent / I2; KOH / 0 - 20 °C
9.1: 63 percent / Amberlyst-15; MeOH / 24 h / 20 °C
10.1: 38 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
11.1: dibutyltin oxide / toluene / 6 h / Heating
11.2: 70 percent / CsF / dimethylformamide / 48 h / 20 °C
12.1: 92 percent / methanol / 0.08 h / 0 °C
With
1H-imidazole; methanol; potassium hydroxide; AD-mix-α; amberlyst-15; borane-THF; pyridine-SO3 complex; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; iodine; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Stille cross-coupling / 7.1: Parikh-Doering oxidation;
DOI:10.1021/ol050975u