Multi-step reaction with 18 steps
1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C
2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C
3.1: imidazole / dimethylformamide / 0 - 20 °C
4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C
5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C
6.2: tetrahydrofuran; hexane / 1 h / -30 °C
6.3: tetrahydrofuran; hexane / -20 °C
7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C
8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C
9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C
10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
17.1: Et3N / benzene / 1 h / 20 °C
18.1: 156 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; lithium hydroxide; n-butyllithium; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; ethanol; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
tetrakis(triphenylphosphine) palladium(0); {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo062089i