Multi-step reaction with 14 steps
1.1: H2 / Pd/CaCO3/Pb / tetrahydrofuran
2.1: NaN3; nBu4NI / dimethylformamide
3.1: 85 percent / nBu4NI; K2CO3 / acetonitrile
4.1: Me3P; H2O / tetrahydrofuran
5.1: iPr2NEt / acetonitrile
6.1: pyridine; DMAP / CH2Cl2
7.1: NaN3 / dimethylformamide / -15 °C
8.1: 74 percent / (NH4)2Ce(NO3)6 / CH2Cl2; 2-methyl-propan-2-ol
9.1: tBuOK
9.2: 70 percent / (Me3Si)2NH
10.1: 95 percent / H2O / acetonitrile / 70 °C
11.1: Me3P; H2O / tetrahydrofuran
12.1: AgNO3; Et3N / acetonitrile
13.1: tetrahydrofuran; acetonitrile / -78 °C
13.2: 82 percent / K2CO3 / methanol
14.1: 57 percent / OsCl3; Na2CO3 / ethyl acetate; acetonitrile; H2O
With
pyridine; dmap; sodium azide; ammonium cerium(IV) nitrate; osmium (III) chloride; potassium tert-butylate; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium carbonate; potassium carbonate; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; trimethylphosphane;
Lindlar's catalyst;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja0608545