Multi-step reaction with 14 steps
1.1: 98 percent / Dess-Martin periodinane / CH2Cl2 / 6 h / 20 °C
2.1: Pichia minuta IAM 12215, yeast
3.1: 99 percent / potassium carbonate / methanol / 5 h / 0 °C
4.1: 100 percent / imidazole / dimethylformamide / 20 °C
5.1: tri-n-butyltin hydride; azobis(isobutyronitrile) / benzene / 12 h / Heating
5.2: 937.2 mg / iodine / CH2Cl2 / 0.5 h / 0 °C
6.1: 97 percent / DDQ / CH2Cl2; H2O / 3 h / 0 °C
7.1: 95 percent / ethyldiisopropylamine; dimethyl sulfoxide; SO3*pyridine / CH2Cl2 / 0.33 h / 0 °C
8.1: 100 percent / 2-methyl-2-butene; sodium dihydrogen phosphate; sodium chlorite / 2-methyl-propan-2-ol; H2O / 20 °C
9.1: Et3N / tetrahydrofuran / 5 h / 20 °C
10.1: 100 percent / DMAP / benzene / 8.5 h / 20 °C
11.1: p-toluenesulfonic acid monohydrate / acetone / 3 h / 20 °C
12.1: 77.0 mg / chromium(II) chloride; nickel(II) chloride / dimethylformamide / 0 - 20 °C
13.1: 95 percent / imidazole / dimethylformamide / 15 h / 20 °C
14.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
14.2: 75 percent / hexamethylphosphoric triamide / tetrahydrofuran; hexane / 1.5 h / -78 - -40 °C
With
1H-imidazole; chromium dichloride; dmap; sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene; pyridine-SO3 complex; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
12.1: Nozaki-Hiyama-Kishi coupling;
DOI:10.1016/j.tet.2007.06.038