Multi-step reaction with 8 steps
1.1: 2-methyl-2-butene; NaH2PO4; NaClO2 / 2-methyl-propan-2-ol; H2O / 1 h / 20 °C
2.1: 3.02 g / trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 2 h / 20 °C
3.2: 62 percent / 4-(dimethylamino)pyridine / toluene / Heating
4.1: potassium hexamethyldisilazanide; hexamethylphosphortriamide / tetrahydrofuran; toluene / 0.5 h / -78 °C
5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C
5.2: Cs2CO3 / PdCl2(dppf)*CH2Cl2 / dimethylformamide; H2O / 16 h / 50 °C
5.3: 86 percent / aq. NAOH; H2O2 / tetrahydrofuran / 0 - 20 °C
6.1: BH3*THF / tetrahydrofuran / 0 °C
6.2: 37 percent / sodium hydroxide; hydrogen peroxide / H2O; tetrahydrofuran / 0.5 h / 20 °C
7.1: 92 percent / tetrapropylammonium perruthenate; 4-methylmorpholine 4-oxide / CH2Cl2 / 1 h / 20 °C
8.1: 48 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 110 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; borane-THF; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;
5.2: Suzuki-Miyaura coupling;
DOI:10.1021/ol025814u