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