Multi-step reaction with 15 steps
1.1: 88 percent / TiCl4 / CH2Cl2 / 8 h / -78 °C
2.1: 87 percent / Proton Sponge(R) / CH2Cl2 / 15 h / 0 - 25 °C
3.1: O3; pyridine / methanol / 0.17 h / -78 °C
3.2: methylsulfide / methanol / 10 h / 25 °C
4.1: 1.18 g / CrCl2 / tetrahydrofuran / 20 °C
5.1: 88 percent / NiCl2; CrCl2 / tetrahydrofuran; dimethylsulfoxide / 20 °C
6.1: NaNO2; H2 / PtO2 / ethyl acetate; ethanol / 3 h / 3040.2 Torr
7.1: DIBAL-H / CH2Cl2; hexane / 2 h / -78 °C
8.1: 411 mg / Dess-Martin periodinane; pyridine / CH2Cl2 / 1.5 h / 20 °C
9.1: 87 percent / aq. DDQ / CH2Cl2 / 0.75 h / 20 °C
10.1: 82 percent / DMAP / CH2Cl2 / 0.5 h / 0 °C
11.1: triethylphosphine / dimethylformamide / 0.5 h / 20 °C
11.2: 86 percent / DBU / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C
12.1: 65 percent / PPTS / ethanol / 22 h / 50 °C
13.1: 2,4,6-trichlorobenzoyl chloride; diisopropylethyl amine / benzene / 10 h / 20 °C
13.2: 66 percent / DMAP / benzene
14.1: PPTS / acetone; H2O / 120 h / Heating
15.1: 10.7 mg / PPTS; 4 Angstroem molecular sieves / benzene / Heating
With
pyridine; chromium dichloride; dmap; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; sodium nitrite; triethylphosphine;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
4.1: Takai olefination / 11.1: Schlosser-Wittig olefination / 13.1: Yonemitsu/Yamaguchi reaction;
DOI:10.1021/ja002377a