Multi-step reaction with 7 steps
1: H2 / 10percent Pd/C / ethanol; acetic acid / 10 h
2: Et3N / tetrahydrofuran / 1.) 78 deg C, 15 min; 2.) 0 deg C, 45 min
3: 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
4: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 2 min
5: 1.) titanium tetraisopropoxide / 2.) 70 deg C, 2 h
6: H2 / Raney Ni / CH2Cl2; acetic acid / 6.5 h
7: trifluoroacetic acid, thioanisole / CH2Cl2 / 1 h / 0 deg C --> room temp.
With
titanium(IV) isopropylate; n-butyllithium; methyl-phenyl-thioether; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; triethylamine; trifluoroacetic acid;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1021/ja00185a042