Multi-step reaction with 7 steps
1: 1) n-BuLi, N,N,N',N'-tetramethylethylenediamine, Ti(O-iPr)4 / 1) ether, -78 deg C, 0.5 h, 2a) -78 deg C, 0.5 h, 2b) to 0 deg C
2: 1) Hg(OAc)2, MeSO3H, 2) meta-chloroperbenzoic acid, BF3*Et2O / 1) MeOH, 0 to 20 deg C, 15 h, 2) CH2Cl2
3: H2 / 10percent Pd/C / propan-2-ol; tetrahydrofuran; H2O / 16 h / 25 °C
4: Et3N / CH2Cl2
5: 1) Me3Al / 1) CH3-CCl3, 60 to 20 deg C, 1 h, 2) CH3-CCl3, 60 deg C, 4 h
6: 71 percent / K2Cr2O7, Bu4NHSO4, 30percent H2SO4 / CH2Cl2 / 0.33 h / 25 °C
7: 69 percent / LiBH4 / tetrahydrofuran / 2 h / -78 °C
With
titanium(IV) isopropylate; potassium dichromate; lithium borohydride; n-butyllithium; methanesulfonic acid; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; boron trifluoride diethyl etherate; mercury(II) diacetate; hydrogen; trimethylaluminum; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; isopropyl alcohol;