Multi-step reaction with 15 steps
1.1: 3.00 g / tetrahydrofuran; toluene / 1 h / 0 °C
2.1: 92 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C
3.1: t-butyllithium / diethyl ether; pentane / 4 h / 0 °C
3.2: 98 percent / diethyl ether; pentane / 0.5 h / 0 °C
4.1: 73 percent / Grubb's second generation catalyst / CH2Cl2 / 40 °C
5.1: 80 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
6.1: 77 percent / cesium carbonate / CH2Cl2 / 2 h / 20 °C
7.1: 86 percent / morpholine / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 0.08 h / 20 °C
8.1: 99 percent / LiAlH[OC(C2H5)3]3 / tetrahydrofuran / 1 h / 0 °C
9.1: 71 percent / diisopropylethylamine / CH2Cl2 / 16 h / 20 °C
10.1: 28 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / Heating
11.1: 96 percent / Ne4NHB(OAc)3; acetic acid / acetonitrile / 19 h / -20 - 0 °C
12.1: 93 percent / camphorsulfonic acid / acetone / 1 h / 20 °C
13.1: 86 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.33 h / Heating
14.1: 100 percent Turnov. / triethylamine / CH2Cl2 / 3 h / 20 °C
15.1: 71 percent / 2,6-di-tert-butylpyridine / CH2Cl2 / 9 h / 20 °C
With
morpholine; 2,6-di-tert-butyl-pyridine; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; Ne4NHB(OAc)3; camphor-10-sulfonic acid; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; acetonitrile; pentane;
1.1: Wittig reaction / 10.1: aldol condensation / 13.1: aldol condensation;
DOI:10.1139/v05-042