Multi-step reaction with 6 steps
1: 1.) n-BuLi; 3.) Ac2O, DMAP; 4.) 6percent HgNa / 1.) THF, hexane, -78 deg C, 45 min; 2.) THF, hexane, -78 deg C, 1 h; 3.) r.t., 4 h; 4.) MeOH, AcOEt, -50 deg C, 6 h
2: 1.) OsO4, NMO; 2.) PPTS / 1.) acetone, water, r.t., 2 h; 2.) MeOH, CH2Cl2, r.t., 2 d
3: 81 percent / NaH / dimethylformamide / Ambient temperature
4: 96 percent / DIBAH / CH2Cl2; hexane / 0.5 h / -78 °C
5: 76 percent / (COCl)2, DMSO, Huenig base / CH2Cl2 / 2 h / -78 - -20 °C
6: 100 percent / KMnO4, KH2PO4 / 2-methyl-propan-2-ol; H2O / 0.25 h / 0 °C
With
dmap; potassium permanganate; potassium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; sodium amalgam; oxalyl dichloride; pyridinium p-toluenesulfonate; acetic anhydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)10758-4