Multi-step reaction with 11 steps
1: 1.) 4A molecular sieves, L-(+)-DIPT, TBHP, Ti(O-i-Pr)4, 2.) P(OEt)3, 3.) Ti(O-i-Pr)4
2: aq. NaHCO3 / acetone / 3 h / Ambient temperature
3: 91.1 percent / PTS, NaHCO3 / CH2Cl2
4: 74.9 percent / water, K3Fe(CN)6, K2CO3, OsO4 / 2-methyl-propan-2-ol / Ambient temperature
5: Et3N / CH2Cl2 / 0 °C
6: K2CO3 / methanol / 0.33 h
7: 85.2 percent / CuI / tetrahydrofuran / -10 °C
8: DIBAL / toluene / 3 h / -78 °C
9: PPh3, DEAD / CH2Cl2 / Ambient temperature
10: 80 percent / 2N aq. HCl / tetrahydrofuran
11: 89 percent / imidazole / dimethylformamide / 0.83 h / Ambient temperature
With
1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; copper(l) iodide; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; triethyl phosphite;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;