Multi-step reaction with 14 steps
1: Et3N / CH2Cl2 / 0.33 h / 0 °C
2: methanol; tetrahydrofuran / 0.5 h / 0 °C
3: pyridinium chlorochromate, 3 Angstroem sieves, acetic acid / 1.) 0 deg C, 4 h, 2.) 24 deg C, 1.5 h
4: Et3N / methanol; tetrahydrofuran / 0.25 h / 24 °C
5: NaBH4 / methanol; tetrahydrofuran / 1 h / 0 °C
6: 85 percent / i-Pr2NEt / tetrahydrofuran / 12 h / 45 °C
7: 76 percent / diisobutylaluminium hydride / toluene / 3 h / -78 °C
8: 65 percent / Bu3P / tetrahydrofuran / 0.75 h / 0 °C
9: 1.) NaIO4, 2.) KH / 1.) 1,4-dioxane, 0 deg C, 6 h, 2.) THF, 12 h
10: 92 percent / n-Bu4NF / hexamethylphosphoric acid triamide / 1.08 h / 105 °C
11: Na2CO3 / CH2Cl2 / 1 h / -78 °C
12: m-ClC6H4CO3H, C5H5N / 1.) -78 deg C, 2.) 0 deg C, 0.5 h
13: 65 percent / 18-crown-6 / toluene / 0.33 h / 0 °C
14: 1.) BH3, 2.) 3-chloroperoxybenzoic acid / 1.) THF, from 0 to 24 deg C, 2.75 h, 2.) 25 deg C, 14 h
With
pyridine; sodium tetrahydroborate; sodium periodate; 18-crown-6 ether; tributylphosphine; 3 A molecular sieve; borane; tetrabutyl ammonium fluoride; potassium hydride; diisobutylaluminium hydride; sodium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;
DOI:10.1039/c39900000953