Multi-step reaction with 10 steps
1: 94 percent / imidazole / dimethylformamide / 1 h / 0 °C
2: 75 percent / m-CPBA / CH2Cl2 / 12 h / 25 °C
3: 86 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 / 6 h / 25 °C
4: 80 percent / NaI, NaOAc, AcOH / acetone / 0.17 h / 25 °C
5: 74 percent / BF3*Et2O / CH2Cl2 / 1 h / -78 °C
6: 94 percent / Et3N, DMAP / CH2Cl2 / 2 h / 25 °C
7: 95 percent / TBAF / tetrahydrofuran / 3 h / 25 °C
8: 85 percent / Et3N, SO3*pyr / dimethylsulfoxide; CH2Cl2 / 1 h / 0 °C
9: 74 percent / n-BuLi, HMPA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; 25 deg C, 12 h
10: 98 percent / TBAF / tetrahydrofuran / 12 h / 25 °C
With
1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dipyridinium dichromate; n-butyllithium; pyridine-SO3 complex; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium acetate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N