Multi-step reaction with 10 steps
1.1: NaHMDS / tetrahydrofuran / 0.08 h / -78 °C
1.2: Davis oxaziridine / tetrahydrofuran / 0.08 h / -78 °C
2.1: 0.313 g / Mg(OMe)2 / 0.5 h / 0 °C
3.1: 86 percent / imidazole; 4-DMAP / CH2Cl2 / 16 h / 25 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
4.2: 92 percent / tetrahydrofuran; hexane / 1 h / -78 °C
5.1: LiCl / acetonitrile / 0.17 h / 25 °C
5.2: i-Pr2NEt / acetonitrile / 0.17 h / 25 °C
5.3: 97 percent / acetonitrile / 36 h / 25 °C
6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / 25 °C
6.2: 94 percent / tetrahydrofuran; toluene / -78 - 25 °C
7.1: 87 percent / PPTS / ethanol / 20 h / 45 °C
8.1: 79 percent / TsOH*H2O / methanol / 16 h / 25 °C
9.1: 77 percent / Et3N; 4-DMAP / CH2Cl2 / 16 h / 25 °C
10.1: 31 percent / (-)-(S,S)-diisopropyl D-tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(Oi-Pr)4 / CH2Cl2; decane / 1.25 h / -25 °C
With
1H-imidazole; tert.-butylhydroperoxide; dmap; n-butyllithium; 4 A molecular sieve; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; toluene-4-sulfonic acid; magnesium methanolate; triethylamine; lithium chloride;
titanium(IV) isopropylate;
In
tetrahydrofuran; methanol; decane; ethanol; hexane; dichloromethane; toluene; acetonitrile;
5.1: Horner-Wadsworth-Emmons olefination / 6.2: Wittig methylenation / 10.1: Katsuki-Sharpless epoxidation;
DOI:10.1039/b602021f