Multi-step reaction with 16 steps
1: 91 percent / K2CO3, CuO / pyridine / 24 h / 145 °C
2: H2 / 10percent Pd/C / ethanol; acetic acid / 10 h
3: Et3N / tetrahydrofuran / 1.) 78 deg C, 15 min; 2.) 0 deg C, 45 min
4: 1.) n-BuLi / 1.) hexane, THF, -78 deg C; 2.) hexane, THF, -78 deg C, 15 min and then to room temp., 1.5 h
5: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 2 min
6: 1.) titanium tetraisopropoxide / 2.) 70 deg C, 2 h
7: H2 / Raney Ni / CH2Cl2; acetic acid / 6.5 h
8: trifluoroacetic acid, thioanisole / CH2Cl2 / 1 h / 0 deg C --> room temp.
10: Et3N / tetrahydrofuran / 0.33 h / 0 °C
11: 1.) n-BuLi / 1.) THF, hexanes, 2.) -78 deg C, 20 min
12: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 20 min; 2.) THF, toluene, -78 deg C, 1.5 min
13: aq. LiOOH / tetrahydrofuran / 1 h / 0 °C
14: diethyl ether / 0.25 h
15: H2 / 10percent Pd/C / diethyl ether; methanol; acetic acid / 0.5 h
16: NaHCO3 / H2O; dioxane / 3 h / Ambient temperature
With
titanium(IV) isopropylate; n-butyllithium; lithium hydroperoxide; methyl-phenyl-thioether; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; trifluoroacetic acid; copper(II) oxide;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid;
DOI:10.1021/ja00185a042