Multi-step reaction with 25 steps
1: 90 percent / CSA / 2 h / 25 °C
2: 91 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C
3: 98 percent / H2 / 10percent Pd/C / ethanol / 24 h / 25 °C
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) r.t., 2 h
5: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) 25 deg C, 2 h
6: Pd(OAc)2 / acetonitrile / 24 h / 50 °C
7: 95 percent / LiBH4, CeCl3*7H2O / tetrahydrofuran; methanol / 1 h / -78 °C
8: 2.) LiEt3BH / 1.) xylene, reflux, 48 h, 2.) THF, r.t., 2 h
9: 100 percent / H2 / 10percent Pd/C / ethanol / 16 h / 25 °C
10: 1.) o-O2NC6H4SeCN, n-Bu3P, 2.) 30percent aq. H2O2 / 1.) THF, 25 deg C, 3 h, 2.) THF, 25 deg C, 6 h
11: 1.) O3, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 2.) 25 deg C, overnight
12: 95 percent / LiCl, (i-Pr)2NEt / acetonitrile / 1.) 25 deg C, 15 min, 2.) 25 deg C, 6 h
13: Et3SiH / Rh(PPh3)3Cl / 2 h / 50 °C
14: 49percent aq. HF / acetonitrile / 3 h / 25 °C
15: imidazole / dimethylformamide / 16 h / 25 °C
17: 98 percent / aq. LiBH4 / diethyl ether; tetrahydrofuran / 1 h / 25 °C
18: 91 percent / Et3N, DMAP / CH2Cl2 / 24 h / 25 °C
19: 91 percent / LiEt3BH / tetrahydrofuran / 2.5 h / 25 °C
20: 85 percent / 4-pyrrolidinopyridine, (i-Pr)2NEt, 1,3-diisopropylcarbodiimide / CH2Cl2 / 24 h / -20 °C
21: aq. 4-methylmorpholine-N-oxide, OsO4 / acetone / 16 h / 25 °C
22: Pb(OAc)4, Na2CO3 / benzene / 1.5 h / 25 °C
23: 94 percent / CrCl2 / tetrahydrofuran; dioxane / 1.5 h / 25 °C
24: 94 percent / DDQ, H2O / CHCl3 / 1 h / 25 °C
25: 1.) 2,6-lutidine , 2.) SiO2 / 1.) CH2Cl2, 0 deg C, 30 min, 2.) 25 deg C, 16 h
With
1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; lead(IV) acetate; triethylsilane; dmap; palladium diacetate; osmium(VIII) oxide; lithium borohydride; ortho-nitrophenyl selenocyanate; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; tributylphosphine; camphor-10-sulfonic acid; hydrogen fluoride; water; hydrogen; dihydrogen peroxide; silica gel; lithium triethylborohydride; sodium carbonate; 4-pyrrolidin-1-ylpyridine; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; diisopropyl-carbodiimide; lithium diisopropyl amide;
palladium on activated charcoal; Wilkinson's catalyst;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;