Multi-step reaction with 9 steps
1: toluene / 1.5 h / -42 °C
2: 2.) oxalic acid / 1.) THF, -78 deg C, 4 h, 2.) H2O, room temperature, overnight
3: 1.) NaIO4, OsO4, 2.) L-Selectride, 3.) NaBO3*4H2O / 1.) H2O, THF, room temperature, 19 h, 2.) THF, -78 deg C, 1 h, 3.) -78 deg C to room temperature, 3 h
4: 1.) NaOMe, 2.) 10percent HCl / 1.) MeOH, reflux, 3.5 h, 2.) room temperature, 15 min
5: 79 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C
6: 94 percent / PPh3, NCS / CH2Cl2 / 1.) -42 deg C, 30 min, 2.) room temperature, 4 h
7: 96 percent / LHMDS / tetrahydrofuran / 2 h / -78 °C
8: 89 percent / CuBr*SMe2, BF3*OEt2 / tetrahydrofuran / 2 h / -78 °C
9: 87 percent / LHMDS / tetrahydrofuran / 2 h / -78 °C
With
hydrogenchloride; sodium perborate; sodium periodate; N-chloro-succinimide; osmium(VIII) oxide; n-butyllithium; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; sodium methylate; oxalic acid; L-Selectride; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo971448u