Multi-step reaction with 16 steps
1: aq. HBr / 0.5 h / Ambient temperature
2: NaH / dimethylformamide / 1 h / Ambient temperature
3: O3; dimethyl sulfide / CH2Cl2; methanol / 1.5 h / -78 °C
4: 60 percent / 3-quinuclidinol / neat (no solvent) / 48 h / Ambient temperature
5: 76 percent / NBS, dimethylsulfide / CH2Cl2; toluene / 15 h / Ambient temperature
6: 92 percent / zinc dust / dimethylformamide / 2 h / Ambient temperature
7: DIBAL-H / toluene; methanol / -78 - 0 °C
8: triethylamine / CH2Cl2 / 0.25 h / 0 °C
9: conc. HCl, acetic acid / acetonitrile / 0.5 h / 0 °C
10: imidazole / dimethylformamide / 0.33 h / 0 °C
11: 1.) O3; 2.) dimethylsulfide / 1.) CH2Cl2, CH3OH, -78 deg C, 40 min
12: 87 percent / 4 Angstroem molecular sieves / toluene / 3 h / Heating
13: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C
14: 2,6-lutidine, NaBr / tetrahydrofuran / 1 h / Ambient temperature
15: 59 percent / NaOMe / methanol / 3 h / 0 °C
16: toluene / 3 h / Heating
With
1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; thionyl chloride; dimethylsulfide; 4 A molecular sieve; hydrogen bromide; sodium methylate; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; triethylamine; 3-quinuclidinol; sodium bromide; zinc;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.3987/COM-98-8302