Multi-step reaction with 10 steps
1: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) -78 deg C, 45 min, 2.) -50 deg C
2: toluene / 12 h / 50 °C
3: DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C
4: (-)-DET, Ti(i-PrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2; toluene / 19 h / -20 °C
6: imidazole / CH2Cl2 / 1 h / Ambient temperature
7: DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C
8: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 45 min, 2.) -50 deg C
9: tetrahydrofuran / 15 h / -78 °C
10: 86 percent / 1 M potassium phosphate buffer, DDQ / CH2Cl2 / 0.17 h / Ambient temperature
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; potassium phosphate buffer; 4 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; hexane; dichloromethane; toluene;