Multi-step reaction with 8 steps
1: 50 percent / Pb(OAc)4, TFA / CH2Cl2 / 3 h / Ambient temperature
2: 60 percent / Rexyn 101 (H) cation-exchange resin, CaSO4 / CH2Cl2 / 24 h / Ambient temperature
3: 95 percent / H2 / 10percent Pd/C / methanol / 6 h / Ambient temperature
4: 80 percent / Et3N / CH2Cl2 / 1 h
5: 40 percent / 4 M HCl / acetone / 24 h / Ambient temperature
6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 4 h
7: 95 percent / H2 / 10percent Pd/C / methanol / 1.5 h
8: 80 percent / Et3N / CH2Cl2 / Ambient temperature
With
lead(IV) acetate; hydrogenchloride; calcium sulfate; n-butyllithium; Rexyn 101 (H) cation-exchange resin; hydrogen; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; dichloromethane; acetone;
DOI:10.1021/ja00014a039