Multi-step reaction with 8 steps
1.1: 84 percent / AlMe3 / CH2Cl2 / -10 °C
2.1: tetrahydrofuran; toluene / 2.5 h / -78 - -5 °C
3.1: 73 percent / CeCl3*7H2O; NaBH4 / methanol / 0.17 h / -78 °C
4.1: 89 percent / RuCl2(CHPh)(PCy3)IMesH2 / CH2Cl2 / 0.33 h / Heating
5.1: 90 percent / BnEt3NCl; aq. KOH / toluene / 24 h / 50 °C
6.1: 88 percent / K2OsO4*2H2O; K2CO3; K3Fe(CN)6 / methanesulfonamide; quinuclidine / 2-methyl-propan-2-ol; H2O / 18 h / 20 °C
7.1: Bu2SnO / toluene / 3 h / Heating
7.2: 91 percent / tetrabutylammonium iodide / toluene / 12 h / 60 °C
8.1: 96 percent / N,N-dimethylaminopyridine; diisopropylethylamine / CH2Cl2 / 24 h / 23 °C
With
dmap; potassium hydroxide; sodium tetrahydroborate; potassium osmate(VI); cerium(III) chloride; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; di(n-butyl)tin oxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III);
Quinuclidine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanesulfonamide;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
3.1: Luche reduction;
DOI:10.1021/ol025680k