Multi-step reaction with 16 steps
1.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C
2.1: O3 / CH2Cl2 / -78 °C
2.2: PPh3 / CH2Cl2 / 1 h / -78 - 25 °C
3.1: 28.9 g / benzene / 40 h / 70 °C
4.1: 96 percent / DIBAL-H / toluene; tetrahydrofuran / 2.5 h / -78 °C
5.1: TsOH*H2O / acetone / 3 h / 25 °C
6.1: 25.84 g / imidazole; 4-DMAP / CH2Cl2 / 1.5 h / 25 °C
7.1: 78 percent / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 25 °C
8.1: 97 percent / K2CO3 / acetone / 16 h / 25 °C
9.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
9.2: Davis oxaziridine / tetrahydrofuran; toluene / 1 h / -78 °C
10.1: 86 percent / imidazole; 4-DMAP / CH2Cl2 / 16 h / 25 °C
11.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
11.2: 92 percent / tetrahydrofuran; hexane / 1 h / -78 °C
12.1: LiCl / acetonitrile / 0.17 h / 25 °C
12.2: i-Pr2NEt / acetonitrile / 0.17 h / 25 °C
12.3: 97 percent / acetonitrile / 36 h / 25 °C
13.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / 25 °C
13.2: 94 percent / tetrahydrofuran; toluene / -78 - 25 °C
14.1: 87 percent / PPTS / ethanol / 20 h / 45 °C
15.1: 79 percent / TsOH*H2O / methanol / 16 h / 25 °C
16.1: 77 percent / Et3N; 4-DMAP / CH2Cl2 / 16 h / 25 °C
With
1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; lithium chloride;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;
3.1: Wittig reaction / 12.1: Horner-Wadsworth-Emmons olefination / 13.2: Wittig methylenation;
DOI:10.1039/b602021f