Multi-step reaction with 22 steps
1: 99 percent / CuBr-Me2S complex, HMPA / tetrahydrofuran / 1 h / -78 °C
2: 1.) MeLi / 1.) THF, -20 deg C, 0.5 h, 2.) THF, -20 deg, overnight
3: 87 percent / triethylamine, triphenylphosphine, palladium acetate / dimethylformamide / 3 h / 760 Torr
4: 85 percent / p-toluenesulfonic acid / acetone / 36 h / Ambient temperature
5: 1). potasium tert-butoxide 2.)K2CO3 / 1.) benzene, RT, 10 min, 2.) MeOH, overnight
6: 93 percent / p-toluenesulfonic acid, pyridine / methanol / 8 h
7: 1.) N-methylomorpholine N-oxide, N-methylmorpholine, 4 Angstroem molecular sieves , 2.) tetrapropylamoniumperruthenate / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, overnight
8: LDA / tetrahydrofuran
9: NBS, propylene oxide, Et3N
10: 78 percent / 30percent H2O2, 1 N NaOH / CH2Cl2; methanol / 2 h / -10 - 10 °C
11: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h
12: amonium formate, Pd2(dba)3*CHCl3, tributylphosphine / dioxane / 1 h / Heating
13: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,
14: 1.) 1,7 M tert-butyllithium / 1.) THF, pentane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h
15: 1). pyridine 2). p-cymene / 1). THF, methylene dichloride, toluene, from -40 deg C to RT 1.5 h, 2). 130 deg C, 90 min
16: 91 percent / 1 M TBAF / tetrahydrofuran
17: NaHCO3, m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature
18: 1.) 97 percent N-methylmorpholine N-oxide, 4 Angstroem molecular sieves, N-methylmorpholine, 2.) tetrapropyloamonium perruthenate / 1.) CH2Cl, 15 min., 2.) CH2Cl2, RT, 30 min.,
19: 92 percent / H2 / 10 percent Pd/C / ethyl acetate / 0.25 h / 760 Torr
20: 90 percent / 1 M superhydride / CH2Cl2; tetrahydrofuran / 0.17 h / -78 °C
21: 93 percent / imidazole, DMAP / dimethylformamide / 0.5 h
22: 85 percent / 1 M superhydride / CH2Cl2; tetrahydrofuran / -78 - 20 °C
With
4-methyl-morpholine; pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hydroxide; N-Bromosuccinimide; tetrapropylammonium perruthennate; tributylphosphine; 4-methylisopropylbenzene; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; methyllithium; hydrogen; dihydrogen peroxide; tert.-butyl lithium; ammonium formate; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; methyloxirane; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja9533454