Multi-step reaction with 19 steps
1: 99 percent / LiAlH4 / diethyl ether / 0.08 h / 0 deg C to r.t.
2: 98 percent / pyridine / Ambient temperature
3: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 6 h / Ambient temperature
4: 98 percent / d-camphorsulfonic acid / benzene / 0.5 h / Ambient temperature
5: 96 percent / LiAlH4 / diethyl ether / 1 h / 0 deg C to r.t.
6: 96 percent / pyridine / 2 h / Ambient temperature
7: 94 percent / NaI / acetone / 8 h / Heating
8: 93 percent / dimethylformamide / 6 h / 60 °C
9: 1) n-BuLi / 1) Et2O, hexane, 15 min, r.t., 2) Et2O, hexane, -75 deg C, 2 h
10: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 1 h, 2) 3 h
11: 84 percent / Al-Hg / tetrahydrofuran; H2O / 3 h / Ambient temperature
12: 1) n-BuLi / 1) Et2O, hexane, -78 deg C, 30 min, 2) Et2O, 2 h
13: 100 percent / LiAlH4 / tetrahydrofuran / 0 °C
14: d-camphorsulfonic acid / benzene / Ambient temperature; 1) 30 sec, sonication, 2) 3 h
15: 98 percent / imidazole / CH2Cl2 / 3 h / Ambient temperature
16: 1) OsO4, N-methylmorpholine oxide, 2) Na2S2O4, Celite / 1) acetone, H2O, 6 h, r.t., 2) H2O, acetone, overnight, r.t.
17: 95 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature
18: 1) n-BuLi / 1) hexane, THF, 0 deg C, 1 h, 2) THF, r.t., overnight
19: 99 percent / n-Bu4NF / tetrahydrofuran / 12 h / Ambient temperature
With
pyridine; 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium dithionite; oxalyl dichloride; aluminium amalgam; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(01)87185-4