Multi-step reaction with 18 steps
1.1: 93 percent / NaHCO3; KI; I2 / H2O / 20 °C
2.1: 94 percent / DBU / tetrahydrofuran / Heating
3.1: 93 percent / NaHCO3 / Heating
4.1: Novozym 435 / various solvent(s) / 20 °C
4.2: 14.5 g / lithium aluminum hydride / tetrahydrofuran / 0 °C
5.1: 14 percent / imidazole / dimethylformamide / 0 °C
6.1: mCPBA / CH2Cl2 / 0 °C
7.1: 98 percent / pyridine / 0 °C
8.1: 0 °C
9.1: DBU / 120 h / 80 °C
10.1: HCl / H2O / 20 °C
11.1: NaOMe / methanol / 20 °C
12.1: 99 percent / diisopropylethylamine / CH2Cl2 / 40 °C
13.1: 99 percent / OsO4; N-methylmorpholine N-oxide / acetone; H2O / 20 °C
14.1: triethylamine; Me2SnCl2 / 0 °C
15.1: 94 percent / PCC; molecular sieve 4 Angstroem / CH2Cl2 / Heating
16.1: NaBH4 / CH2Cl2; methanol / 0 °C
17.1: 83 percent / pyridine / H2O / 100 °C
18.1: 95 percent / PCC; molecular sieve 4 Angstroem / CH2Cl2 / Heating
With
pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; Novozym 435; 4 A molecular sieve; iodine; sodium methylate; dimethyltin dichloride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; potassium iodide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tetasy.2003.12.042