Multi-step reaction with 16 steps
1.1: 6.16 g / imidazole; 4-(dimethylamino)pyridine / CH2Cl2
2.1: 98 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C
3.1: BF3*OEt2 / tetrahydrofuran; hexane / 3.33 h
3.2: 1.6 g / H2O2; NaOH / tetrahydrofuran; hexane; H2O / 1 h / Heating
4.1: imidazole; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C
5.1: CSA / CH2Cl2; methanol / 4 h / 20 °C
6.1: 99 percent / NaH; N-(2,4,6-triisopropylbenzenesulfonyl)imidazole / tetrahydrofuran / 0 - 20 °C
7.1: t-BuLi / diethyl ether / 1 h / -78 - -45 °C
7.2: diethyl ether / 2 h / -78 - -20 °C
7.3: 60 mg / tetrahydrofuran; 1,2-dimethoxy-ethane / 2 h / -78 - 0 °C
8.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C
9.1: triethylamine / tetrahydrofuran / 0 - 20 °C
10.1: K2CO3 / methanol / 12 h / 20 °C
11.1: 0.634 g / Na-Hg; Na2HPO4 / methanol / 32 h
12.1: 83 percent / HCl / acetone / 24 h
13.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C
14.1: 0.047 g / second generation Grubbs catalyst / benzene / 65 °C
15.1: 96 percent / NaBH4 / methanol / 0.5 h / 0 °C
16.1: 86 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C
With
1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; benzene;
DOI:10.1021/jo052314g