Multi-step reaction with 13 steps
1: 74 percent / LDA / tetrahydrofuran / -78 °C
2: NaBH4 / methanol / 0 °C
3: pyridine / 0 °C
4: DBU / toluene / 100 °C
5: 1.) O3, pyridine, Me2S; 2.) NaBH4 / 1.) CH2Cl2, MeOH, -78 deg C; 2.) 0 deg C
6: 99 percent / i-Pr2NEt / 1,2-dichloro-ethane / 50 °C
7: 88 percent / LiAlH4 / tetrahydrofuran / 0 °C
8: 75 percent / pyridine / 0 °C
9: imidazole / dimethylformamide / Ambient temperature
10: DIBAL-H / toluene / -78 °C
11: PDC, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature
12: 1.) K2CO3; 2.) NaBH4 / 1.) MeOH, RT; 2.) MeOH, 0 deg C
13: 96 percent / Bu3P / pyridine / Ambient temperature
With
pyridine; 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; dimethylsulfide; tributylphosphine; 4 A molecular sieve; diisobutylaluminium hydride; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0040-4039(96)01585-7