Multi-step reaction with 9 steps
1.1: 82 percent / DMAP / pyridine; CH2Cl2 / 20 °C
2.1: 91 percent / TFA; triethylsilane / CH2Cl2 / 3 h / 0 - 20 °C
3.1: triflic anhydride; pyridine / 1,2-dichloro-ethane / 1.5 h / -15 °C
3.2: 82 percent / H2O / 0.5 h / 80 °C
4.1: 100 percent / NaOMe / methanol / 3 h / 20 °C
5.1: 10-dl-camphorsulfonic acid / toluene / 1 h / 20 °C
5.2: 86 percent / aq. AcOH / 0.17 h / 20 °C
6.1: 79 percent / Me3SiOTf / CH2Cl2; toluene / 0.5 h / 0 °C
7.1: aq. AcOH / 100 °C
8.1: calcium hypochlorite; NaHCO3; TEMPO / KBr / H2O; CH2Cl2; acetonitrile / 0.75 h / 0 °C
9.1: 3.80 g / dimethylformamide / 1 h / 50 °C
With
pyridine; triethylsilane; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; calcium hypochlorite; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid;
potassium bromide;
In
pyridine; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;
4.1: Zemplen reaction;
DOI:10.1016/S0008-6215(02)00060-5