Multi-step reaction with 22 steps
1: 1.) 2,6-lutidine / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 30 min
2: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min
3: 90 percent / p-TsOH*H2O / CHCl3 / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h
4: 92 percent / NaBH4 / methanol; CH2Cl2 / 2 h / -78 °C
5: 98 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
6: 98 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7: 92 percent / PPTS / CH2Cl2; methanol / 2 h / -20 °C
8: 96 percent / Et3N, SO3*pyridine / CH2Cl2; dimethylsulfoxide / 3 h / Ambient temperature
9: 63 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min
10: 76 percent / BF3*OEt2 / CHCl3 / 1 h / 0 °C
11: 64 percent / SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide; methanol / 2 h / 0 °C
12: 1.) BF3*OEt2, 2.) PPTS / 1.) CH2Cl2, hexane, -78 deg C, 3 h; -78 deg C to -20 deg C, 1 h, 2.) CH2Cl2, MeOH, room temperature, 2 h
13: 94 percent / AcOH, Bu4NF / tetrahydrofuran / 5 h / Ambient temperature
14: 95 percent / Me4NBH(OAc)3 / acetonitrile; acetic acid / 3 h / -20 °C
15: 1.) 2,6-lutidine / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 30 min
16: 96 percent / n-BuLi, DMPU / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min
17: 90 percent / p-TsOH*H2O / CHCl3 / 3 h / 0 °C
18: 74 percent / BF3*OEt2 / CHCl3 / 0.5 h / Ambient temperature
19: 1.) BF3*OEt2, 2.) PPTS / 1.) CH2Cl2, hexane, -78 deg C, 3 h; -78 deg C to -20 deg C, 1 h, 2.) CH2Cl2, MeOH, room temperature, 2 h
20: 77 percent / toluene / 2 h / -78 °C
21: 97 percent / Bu4NF / tetrahydrofuran / 15 h / Ambient temperature
22: 80 percent / 2,6-lutidine / CH2Cl2 / 3 h / Ambient temperature
With
2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; n-butyllithium; samarium diiodide; pyridine-SO3 complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; acetic acid; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1021/jo980320p