Multi-step reaction with 13 steps
1: 98 percent / PPTS / CH2Cl2 / 4.5 h / Ambient temperature
2: 8.3 g / LiAlH4 / diethyl ether / 1 h / -75 °C
3: 98 percent / pyridine / 12 h
4: p-TsOH / methanol; H2O / 6 h / Ambient temperature
5: 81 percent / PCC / CH2Cl2 / 2.5 h / Ambient temperature
6: 87 percent / diisopropylamine, 2,2'-dipyridyl, n-BuLi / tetrahydrofuran; hexane / -70 deg C, 30 min., -10 deg C, 1.1 h
7: 88 percent / NaH, triethyl phosphite, O2 / tetrahydrofuran; 2-methyl-propan-2-ol; dimethylformamide / 3 h / -20 - -18 °C
8: 77 percent / lead tetraacetate / benzene; methanol / 4 h / 40 °C
9: 1) phenylselenyl chloride, HCl 2) H2O2 (15percent) / 1) EtOAc, room temp., 1.6 h; 2) CH2Cl2, pyridine, 2.5 h, room temp.
10: 22 mg / NaOH / methanol / 1) 2 h; 2) room temp., 1.5 h
11: MnO2 / CH2Cl2 / 2.5 h / Ambient temperature
12: 1) n-BuLi / 1) hexane, THF, 45 min, -18 deg C; 2) THF, -20 to -18 deg C, 1 h
13: HCl / tetrahydrofuran
With
lead(IV) acetate; hydrogenchloride; [2,2]bipyridinyl; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; Phenylselenyl chloride; dihydrogen peroxide; oxygen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; diisopropylamine; pyridinium chlorochromate; triethyl phosphite;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(01)86076-2