Multi-step reaction with 12 steps
1: 55 percent / NaBH4 / methanol; H2O / 2 h / 0 °C
2: 98 percent / dimethylformamide / 0.25 h / Ambient temperature
3: DIBAL-H / CH2Cl2 / 1 h / -78 °C
4: PDC, mol. sieves 4A / CH2Cl2 / 1 h / Ambient temperature
5: Br2 / CH2Cl2 / 0 °C
6: Et3N / 2 h / Ambient temperature
7: 74 percent / Pd(0)-CuI(I), Et3N / tetrahydrofuran / 1 h / Ambient temperature
8: tetrahydrofuran / -78 °C
9: DMAP / CH2Cl2 / Ambient temperature
10: PPTS / methanol / 14 h / Ambient temperature
11: Ph3P, DEAD / tetrahydrofuran / 1 h / 0 - 20 °C
12: K2CO3, H2O / methanol / 0.25 h / Ambient temperature
With
dmap; sodium tetrahydroborate; copper(l) iodide; dipyridinium dichromate; 4 A molecular sieve; water; bromine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; palladium; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)01834-6