Multi-step reaction with 11 steps
1.1: 100 percent / toluene / 16 h / Heating
2.1: 80 percent / TiCl4; Et3SiH / CH2Cl2 / 16 h / -78 - 20 °C
3.1: 95 percent / SOCl2 / tetrahydrofuran / 0 - 20 °C
4.1: 80 percent / NaOEt / ethanol / 45 °C
5.1: 85 percent / aq. HCl / tetrahydrofuran / Heating
6.1: 75 percent / KH / dimethylformamide / 1 h / 20 °C
7.1: LDA / tetrahydrofuran / -78 °C
7.2: 70 percent / tetrahydrofuran
8.1: ozone / CH2Cl2 / -78 °C
8.2: 90 percent / PS-PPh3 / CH2Cl2
9.1: 90 percent / KMnO4; NaH2PO4 / 2-methyl-propan-2-ol
10.1: 65 percent / EDCI; HOBt / H2O
11.1: 80 percent / Jones reagent / acetone
With
hydrogenchloride; triethylsilane; potassium permanganate; sodium dihydrogenphosphate; thionyl chloride; jones reagent; sodium ethanolate; titanium tetrachloride; potassium hydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.09.001