Multi-step reaction with 17 steps
1.1: 95 percent / Et3SiH; Pd(PPh3)4; LiCl / dimethylformamide / 24 h / 55 °C
2.1: 96 percent / K2OsO4*2H2O; (DHQD)2PHAL; MeSO2NH2 / K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O / 2 h
3.1: 98 percent / Et3N; DMAP / CH2Cl2 / 8 h / 0 - 25 °C
4.1: H2 / Pd(OH)2/C / methanol; H2O / 2 h / 25 °C / pH 7
5.1: base
6.1: NaBH4 / methanol / 0.5 h / 0 - 25 °C
7.1: Pb(OAc)4 / CH2Cl2 / 2 h / 0 - 25 °C
8.1: 70 percent / DBU / toluene / 4 h / Heating
9.1: SOCl2; pyridine / 8 h / 0 - 25 °C
9.2: K2CO3; MeOH / 2 h / 25 °C
10.1: Br2; N,N-dimethylaniline; K2CO3 / CH2Cl2 / 0.17 h / -78 °C
10.2: 76 percent / N,N-dimethylaniline; K2CO3 / CH2Cl2 / 3 h / -78 - 0 °C
11.1: 42 percent / (Me3Si)3SiH; AIBN / toluene / 0.5 h / 110 °C
12.1: 88 percent / NaBH4 / methanol / 0.25 h / 0 °C
13.1: pyridine; DMAP / 5 h / 60 °C
14.1: HCl / methanol; diethyl ether / 4 h / 0 - 25 °C
15.1: 79 percent / Et3N; DMAP / CH2Cl2 / 6 h / 0 - 25 °C
16.1: H2SO4 / CH2Cl2 / 0.5 h / 0 °C
17.1: PCC / 1,2-dichloro-ethane / 16 h / 65 °C
With
pyridine; lead(IV) acetate; hydrogenchloride; triethylsilane; dmap; sodium tetrahydroborate; potassium osmate(VI); tetrakis(triphenylphosphine) palladium(0); thionyl chloride; 2,2'-azobis(isobutyronitrile); methanesulfonamide; tris-(trimethylsilyl)silane; sulfuric acid; hydrogen; bromine; potassium carbonate; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; pyridinium chlorochromate; lithium chloride;
palladium dihydroxide; potassium carbonate; potassium hexacyanoferrate(III);
In
methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1002/anie.200500217