Multi-step reaction with 13 steps
1: 97 percent / BF3-Et2O / 1.67 h / Ambient temperature
2: H2 / Pd-C(5percent) / ethyl acetate / 12 h
3: Et3N, H2O / methanol / Ambient temperature
4: CH2Cl2 / 0 deg C, then room temp., overnight
5: 86 percent / CSA / CH2Cl2 / 1.5 h / Ambient temperature
6: 93 percent / KOH, H2O / methanol / 1.75 h
7: 78 percent / dipyridinium chromate / CH2Cl2 / 0.17 h / Ambient temperature
8: 30 percent / n-BuLi / methanol / -45 °C
9: 95 percent / MCPBA, aq.NaHCO3(sat) / CH2Cl2 / 0 deg C, 1.5 h; room temp., 20 min
10: 1.) LiBr, 2.) KF / 1.) THF, -78 deg C; 2.) MeOH, room temp., 1.5 h
11: 1.) NaH; 2.) imidazole / 1.) THF,-20 deg C, 30 min, then 0 deg C, 15 min; 2.) 40 min
12: 38 percent / n-Bu3SnH, AIBN / 0.33 h / 90 °C
13: ZnCl2, HCl
With
1H-imidazole; hydrogenchloride; potassium fluoride; potassium hydroxide; n-butyllithium; pyridinium dichromate; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; zinc(II) chloride;
5%-palladium/activated carbon;
In
methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(01)90575-7