Multi-step reaction with 15 steps
1: 100 percent / NaBH4 / methanol / 3 h / -20 - -10 °C
2: 92 percent / t-BuOCl, L-(+)-diisopropyl tartrate*Ti(OiPr)4 / CH2Cl2 / -20 °C
3: 71 percent / 0.5N NaOH / 2-methyl-propan-2-ol / Heating
4: POCl3 / CH2Cl2 / Ambient temperature
5: m-chloroperoxybenzoic acid / CH2Cl2 / -78 °C
6: NaOAc / 8 h / Heating
7: 91 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C
8: 88 percent / benzene / Ambient temperature
9: 91 percent / NaBH4 / methanol / -20 - -10 °C
10: 84 percent / t-BuOCl, D-(-)-diisopropyl tartrate, Ti(OiPr)4 / CH2Cl2 / -20 °C
11: 63 percent / 0.5N NaOH / 2-methyl-propan-2-ol / Heating
12: 100 percent / d-10-Camphersulfonic acid / CH2Cl2 / 0.5 h / Ambient temperature
13: 97 percent / m-chloroperoxybenzoic acid / CH2Cl2 / -78 °C
14: 90 percent / NaOAc / Heating
15: 95 percent / diisobutylaluminum hydride / CH2Cl2; hexane / -78 °C
With
titanium(IV) isopropylate; sodium hydroxide; sodium tetrahydroborate; tert-butylhypochlorite; L-(+)-diisopropyl tartrate*Ti(OiPr)4; sodium acetate; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate;
In
methanol; hexane; dichloromethane; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(01)97596-9