Multi-step reaction with 13 steps
1: 87 percent / n-Bu3P / tetrahydrofuran / 18 h / 0 - 25 °C
2: 89 percent / Bio-Rad 50W-X8 cation exchange resin / methanol / 18 h / 25 °C
3: 97 percent / 4-(N,N-dimethylamino)pyridine, Et3N / CH2Cl2 / 18 h / 0 - 25 °C
4: 1.) tert-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, HMPA, from -78 deg C to RT, 75 min
5: 83 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1 h / 0 °C
6: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 - 25 °C
7: 79 percent / pyridinium dichromate, 3-A molecular sieves / CH2Cl2 / 2 h
8: tetrahydrofuran; toluene / 32 h
9: 94 percent / i-Bu2AlH / tetrahydrofuran; CH2Cl2 / 0.67 h / -78 °C
10: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, -78 deg C, 2.) THF, HMPA, from -78 deg C to RT,
11: tetra-n-butylammonium fluoride / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 25 °C
12: PPh3, imidazole, I2 / acetonitrile; diethyl ether / 0.5 h / 0 °C
13: 18-crown-6, potassium hexamethyldisilazide (KHMDS) / tetrahydrofuran; toluene / 10 h / 0 °C
With
1H-imidazole; dmap; dipyridinium dichromate; n-butyllithium; 1,10-Phenanthroline; 18-crown-6 ether; tributylphosphine; 3 A molecular sieve; Bio-Rad 50W-X8 cation exchange resin; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00356a021
