Multi-step reaction with 13 steps
1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 1 h / 20 °C
1.2: 82 percent / tetrahydrofuran / 2 h / 0 °C
2.1: 47 percent / Ti(OiPr)4; D-(-)-diisopropyl tartrate; t-BuOOH / CH2Cl2; decane / 24 h / -20 °C
3.1: 71 percent / VO(acac)2; t-BuOOH / CH2Cl2; decane / 3 h / 20 °C
4.1: CrO3; H2SO4 / acetone / 3 h / 20 °C
5.1: 324 mg / Zn; AcOH / CHCl3 / 3 h / 20 °C
6.1: p-TsOH*H2O / CH2Cl2 / 15 h
7.1: 156 mg / triethylamine / DMAP / CH2Cl2 / 3 h
8.1: 68 percent / TASF / dimethylformamide / 3 h
9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / toluene / 1.5 h / 20 °C
9.2: 54.6 mg / DMAP / toluene / 2 h
10.1: RuCl2(IMes)(PCy3)=CHPh / CH2Cl2 / 4 h / Heating
11.1: 60 mg / H2 / RhCl(PPh3)3 / ethanol / 760 Torr
12.1: TASF; water / acetonitrile / 5 h
13.1: 14 mg / triifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
With
chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; hydrogen; D-(-)-diisopropyl tartrate; magnesium; acetic acid; ethylene dibromide; triethylamine; trifluoroacetic acid; zinc;
dmap; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; RhCl(PPh3)3; toluene-4-sulfonic acid;
In
tetrahydrofuran; decane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
4.1: Jones' oxidation;
DOI:10.1021/ja068901g