Multi-step reaction with 8 steps
1: 90 percent / 2,6-lutidine / tetrahydrofuran / 2 h / -78 °C
2: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min
3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
4: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C
5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C
6: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature
7: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C
8: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature
With
2,6-dimethylpyridine; lithium azide; dimethylsulfide; potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00304a024