Multi-step reaction with 22 steps
1.1: imidazole / dimethylformamide / 3 h / 20 °C
2.1: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C
3.1: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
4.1: 100 percent / I2; PPh3; imidazole / acetonitrile; diethyl ether
5.1: 92 percent / 18-crown-6 / dimethylformamide / 3 h / 20 °C
6.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C
7.1: aq. NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; various solvent(s) / 1 h / 20 °C / pH 7
8.1: TEA; EDCI; HOBt / CH2Cl2
9.1: 90 percent / aq. PPTS / acetone / 1 h / Heating
10.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.33 h / -78 °C
10.2: 100 percent / 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / -78 °C
11.1: aq. H2O2; pyridine; methyltrioxorhenium / CH2Cl2 / 4 h / 0 - 20 °C
11.2: 78 percent / TBAF / CH2Cl2 / 0.5 h / 0 °C
12.1: BF3*OEt2 / CH2Cl2 / 20 °C
13.1: TEA / diethyl ether / 1.5 h / 0 °C
14.1: 3 h / -78 - 0 °C
15.1: 89 percent / PPTS; TMOF / tetrahydrofuran / 0.33 h / 20 °C
16.1: 86 percent / 2,6-lutidine / tetrahydrofuran / 0.33 h / -78 °C
17.1: 96 percent / CeCl3 / tetrahydrofuran / 0.33 h / -78 °C
18.1: TEA / diethyl ether / 3 h / -78 °C
19.1: diethyl ether / 16 h / -78 °C
20.1: imidazole / dimethylformamide / 2 h / 20 °C
21.1: 75 percent / Zn; PbI2; Me3SiCl / TiCl4 / CH2Cl2; tetrahydrofuran / 4 h / 20 °C
22.1: 93 percent / NaI; n-PrI; NaHCO3 / Na2SO3 / acetone / 18 h
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; chloro-trimethyl-silane; cerium(III) chloride; 2-methyl-but-2-ene; 18-crown-6 ether; TEA; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; methyltrioxorhenium(VII); sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-iodo-propane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium iodide; lead(II) iodide; zinc; trimethyl orthoformate;
titanium tetrachloride; sodium sulfite;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1055/s-2005-871960