Multi-step reaction with 12 steps
1: 1.) dimethylaminopyridine (DMAP), 2.) SnCl4 / 1.) CH2Cl2, 25 deg C, 2.) 0 deg C
2: K2CO3 / methanol / 25 °C
3: 1.) n-Bu2SnO, 2.) CsF / 1.) MeOH, 65 deg C, 2 h, 2.) DMF, 25 deg C, 12 h
4: 95 percent / Et3N, dimethylaminopyridine (DMAP) / CH2Cl2 / 2 h / 0 - 25 °C
5: 85 percent / diaminosulphur trifluoride (DAST), N-bromosuccinimide (NBS) / CH2Cl2 / 3 h / -78 - 0 °C
6: 80 percent / AgClO4, SnCl2, 4-A molecular sieves / CH2Cl2 / 12 h / -20 - 0 °C
7: 100 percent / K2CO3 / methanol / 2 h / 25 °C
8: 92 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 - 0 °C
9: 90 percent / di-isobutylaluminium hydride (DIBAL) / CH2Cl2 / 2 h / -78 - 0 °C
10: 75 percent / RuCl3 hydrate, NaIO4 / CCl4; acetonitrile; H2O / 3 h / 0 - 25 °C
11: 90 percent / PhOP(O)Cl2, pyridine / 1,2-dimethoxy-ethane / 1 h / 0 - 25 °C
12: 90 percent / Bu4NF / tetrahydrofuran / 0.5 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; dmap; ruthenium trichloride; sodium periodate; N-Bromosuccinimide; diisobutylaluminum hydride; 4 A molecular sieve; diaminosulphur trifluoride; tetrabutyl ammonium fluoride; silver perchlorate; tin(IV) chloride; di(n-butyl)tin oxide; potassium carbonate; O-phenyl phosphorodichloridate; triethylamine; cesium fluoride; tin(ll) chloride;
In
tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;
DOI:10.1039/c39900001275