Multi-step reaction with 17 steps
1.1: 95 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / 50 °C
2.1: tetrahydrofuran / 1.17 h / -70 °C
3.1: disiamylborane / tetrahydrofuran / 1.17 h / 0 °C
3.2: H2O2; NaHCO3 / tetrahydrofuran; methanol; H2O / 20 °C
4.1: 37.5 g / 10-camphorsulfonic acid / 1,2-dichloro-ethane / 3 h / 20 °C
5.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 24 h / 20 °C
6.1: DMSO; (COCl)2; triethylamine / CH2Cl2 / 2.25 h / -80 - -60 °C
7.1: 4.8 g / toluene / 0.58 h / -80 - -70 °C
8.1: 3.79 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C
9.1: N-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C
10.1: NaIO4 / 2-methyl-propan-2-ol; H2O / 1 h / 20 °C
11.1: 437 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 3 h / 20 °C
12.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; 10-camphorsulfonic acid / CH2Cl2 / 24 h / 35 °C
13.1: 63 percent / tetrahydrofuran / 60 °C
14.1: BH3*THF / tetrahydrofuran / 0 - 20 °C
14.2: 75 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0 - 20 °C
15.1: 57 percent / DMSO; (COCl)2; triethylamine / CH2Cl2 / 1.5 h / -70 - -40 °C
16.1: 58 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 12 h / 20 °C
17.1: 84 percent / trifluoromethanesulfonic acid / hexane / 19 h / 20 °C
With
dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; hydrogen; bis-(1,2-dimethylpropyl)borane; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide;
palladium dihydroxide;
In
tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
6.1: Swern oxidation / 15.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00660-9