Multi-step reaction with 14 steps
1: 89 percent / BF3*Et2O / CH2Cl2 / 72 h / 25 °C
2: NaOMe / methanol; tetrahydrofuran / 1 h / 25 °C
3: 89 percent / TsOH*H2O / dimethylformamide / 24 h / 25 °C
4: 1.) Tf2O, 2,6-di-tert-butyl-4-methylpyridine / 1.) CH2Cl2, -60 deg C, 15 min, 2.) CH2Cl2, from -60 to 0 deg C, 70 min
5: 78 percent / TFA / CH2Cl2 / 1 h / 25 °C
6: 98 percent / LiOH*H2O / methanol; tetrahydrofuran / 168 h / 25 °C
7: 75 percent / 4-dimethylaminopyridine, Et3N / CH2Cl2 / 2 h / 25 °C
8: 1.) 2,6-di-tert-4-methylpyridine, Tf2O / 1.) CH2Cl2, -60 deg C, 15 min, 2.) CH2Cl2, from -60 to -5 deg C, 70 min
9: 77 percent / Hg(OCOCF3)2, H2O / CH2Cl2 / 0.33 h / 25 °C
10: 92 percent / NaH / dimethylformamide / 1 h / 25 °C
11: H2 / Pd/Pb/CaCO3 / ethyl acetate / 760 Torr
12: H2 / Pd/C / ethyl acetate / 8 h / 25 °C / 760 Torr
13: DMAP, Et3N / CH2Cl2 / 0.17 h / 25 °C
14: 97 percent / NaOMe, MeOH / 0.5 h / 25 °C
With
methanol; dmap; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; water; hydrogen; sodium methylate; mercury(II) trifluoroacetate; sodium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid;
palladium on activated charcoal; Lindlar's catalyst; palladium on calcium fluoride poisoned with lead;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ja9608555