Multi-step reaction with 16 steps
1: 100 percent / 2 h / Heating
2: 99 percent / H2 / Pd/C / diethyl ether / 2068.6 Torr
3: 75 percent / PCC, HOAc, Celite, molecular sieve 4A / CH2Cl2
5: 84 percent / KBr, m-CPBA, 18-cr-6 / CH2Cl2 / 0.5 h / 0 °C
6: 98 percent / Mg / tetrahydrofuran
7: 97 percent / NaBH4 / methanol / 0.2 h / Ambient temperature
8: 98 percent / PBr3, pyridine / benzene / 3 h / Ambient temperature
9: 80 percent / 18-cr-6 / acetonitrile / 1 h / 60 °C
10: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, RT, 3 h
11: 1.) BF3-CH3NO2 / 1.) nitromethane, -30 deg C, 2.25 min, 2.) nitromethane, -30 deg C, 2 h
12: 1.) LDA, O2, 2.) 1M SnCl2, 2M HCl / 1.) THF, -78 deg C, 1 h, 2.) THF, 0 deg C
13: 92 percent / m-CPBA / CH2Cl2 / -78 °C
14: 72 percent / trifluoroacetic anhydride, pyridine / CH2Cl2 / 5 h / 0 °C
15: 1.) TiCl4, 2.) H2O / 1.) glac. HOAc, RT, 20 min, 2.) reflux, 1 h
16: 91 percent / BBr3 / CH2Cl2 / 0 - 20 °C
With
pyridine; hydrogenchloride; sodium tetrahydroborate; 18-crown-6 ether; 4 A molecular sieve; Celite; water; hydrogen; oxygen; boron tribromide; phosphorus tribromide; titanium tetrachloride; boron trifluoride nitrometane adduct; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic anhydride; tin(ll) chloride; potassium bromide; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;
DOI:10.1080/00397919108020799