Multi-step reaction with 22 steps
1.1: 3.59 g / imidazole / CH2Cl2 / 1 h / 20 °C
2.1: 98 percent / TEA / CH2Cl2 / 0 - 20 °C
3.1: 84 percent / CSA; methanol / 2 h / 20 °C
4.1: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C
5.1: 98 percent / TEA / CH2Cl2 / 0 - 20 °C
6.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C
7.1: 82 percent / PCC; 4 Angstroem molecular sieves / CH2Cl2 / 2 h / 20 °C
8.1: TiCl4 / CH2Cl2 / 0.25 h / -78 °C
8.2: 95 percent / CH2Cl2 / 0.5 h / -78 °C
9.1: 66 percent / lithium aluminum hydride / diethyl ether / 0 - 20 °C
10.1: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0 - 20 °C
11.1: O3 / CH2Cl2 / 0.17 h / -78 °C
11.2: 97 percent / triphenylphosphine / CH2Cl2 / -78 - 20 °C
12.1: 97 percent / magnesium bromide etherate / CH2Cl2 / 1 h / 20 °C
13.1: O3 / CH2Cl2 / 0.25 h / -78 °C
13.2: triphenylphosphine / CH2Cl2 / -78 - 20 °C
14.1: 851 mg / sodium borohydride / methanol / 0 - 20 °C
15.1: 92 percent / TEA / CH2Cl2 / 14 h / 0 °C
16.1: 89 percent / PPTS / benzene / 2 h / Heating
17.1: 90 percent / NaI / acetone / 2 h / Heating
18.1: 91 percent / n-Bu3SnH; Et3B; air / toluene; hexane / -78 °C
19.1: 100 percent / lithium borohydride / diethyl ether; tetrahydrofuran / 0 - 20 °C
20.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
21.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
22.1: 68.0 mg / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
With
1H-imidazole; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; lithium borohydride; air; triethyl borane; 4 A molecular sieve; TEA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; Dess-Martin periodane; ozone; magnesium bromide ethyl etherate; pyridinium chlorochromate; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
4.1: Williamson ether synthesis / 20.1: Dess-Martin oxidation / 22.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.07.005